Recent Advances in Selective
Reactions Promoted by Barium Reagents

Akira Yanagisawa; Kazuhiro Yoshida

doi:10.1055/s-0031-1289905

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synlett 2011(20): 2929-2938
DOI: 10.1055/s-0031-1289905

ACCOUNT

Recent Advances in Selective Reactions Promoted by Barium Reagents

Akira Yanagisawa*, Kazuhiro Yoshida
Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522, Japan
Fax: +81(43)2902789; e-Mail: ayanagi@faculty.chiba-u.jp;

Further Information

Publication History

Received 27 June 2011
Publication Date:
23 November 2011 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

Since the first report in 1991 of the regio- and stereoselective allylation of carbonyl compounds with allylic barium reagents, various barium reagents have been utilized in organic transformations. This account focuses on recent examples of barium reagent promoted regio- and stereoselective reactions, such as Barbier-type propargylations, a Reformatsky-type reaction, Michael additions, aldol reactions, Mannich-type reactions, a Friedel-Crafts-type alkylation, and a Diels-Alder-type reaction.

1 Introduction

2 Stoichiometric Use of Barium Reagents

2.1 Selective Propargylation of Electrophiles with Propargylic Bromides Promoted by Reactive Barium

2.1.1 Selective Propargylation of Carbonyl Compounds

2.1.2 Selective Propargylation of Imines

2.1.3 Selective Propargylation of Azo Compounds

2.2 Reformatsky-type Reaction of α-Chloro Ketones with Aldehydes Promoted by Reactive Barium

2.3 Barium Hydride Promoted Synthesis of 1,5-Diketones

2.3.1 Homocoupling of Enones

2.3.2 Cross-Coupling of Enones

3 Catalytic Use of Barium Reagents

3.1 Barium Alkoxide Catalyzed Synthesis of 1,5-Diketones

3.1.1 Reactions of Ketones with Aldehydes

3.1.2 Reactions of Ketones with Enones

3.2 Barium Alkoxide Catalyzed Direct Aldol Reaction

3.3 Barium Alkoxide Catalyzed Direct Mannich-type Reaction

3.4 Chiral Barium Alkoxide Catalyzed Asymmetric Friedel-Crafts-type Alkylation

3.5 Chiral Barium Alkoxide Catalyzed Asymmetric Diels-Alder-type Reaction

4 Conclusion

Key words

asymmetric catalysis - barium - cross-coupling - homocoupling - nucleophilic additions

References

For reactions of allylic barium reagents, see:
1a Yanagisawa A. Habaue S. Yamamoto H. J. Am. Chem. Soc. 1991, 113: 8955

Google Scholar
1b Yanagisawa A. Habaue S. Yasue K. Yamamoto H. J. Am. Chem. Soc. 1994, 116: 6130

Google Scholar
For reviews, see:
1c Yanagisawa A. Yamamoto H. In Active Metals. Preparation, Characterization, Applications Fürstner A. VCH; Weinheim: 1996. p.61

Google Scholar
1d Yanagisawa A. In Science of Synthesis Vol. 7: Yamamoto H. Thieme; Stuttgart: 2004. p.695

Google Scholar
1e Yanagisawa A. In Main Group Metals in Organic Synthesis Vol. 1: Yamamoto H. Oshima K. Wiley-VCH; Weinheim: 2004. p.175

Google Scholar
For related strontium reagents, see:
1f Miyoshi N. Kamiura K. Oka H. Kita A. Kuwata R. Ikehara D. Wada M. Bull. Chem. Soc. Jpn. 2004, 77: 341

Google Scholar
1g Miyoshi N. Ikehara D. Kohno T. Matsui A. Wada M. Chem. Lett. 2005, 34: 760

Google Scholar
1h Miyoshi N. In Science of Synthesis Vol. 7: Yamamoto H. Thieme; Stuttgart: 2004. p.685

Google Scholar
1i Miyoshi N. Ikehara D. Matsuo T. Kohno T. Matsui A. Wada M.
J. Synth. Org. Chem., Jpn. 2006, 64: 845

Google Scholar
For reviews on alkaline earth metal reagents, see:
1j Alexander JS. Ruhlandt-Senge K. Eur. J. Inorg. Chem. 2002, 2761

Google Scholar
1k Westerhausen M. Gärtner M. Fischer R. Langer J. Yu L. Reiher M. Chem. Eur. J. 2007, 13: 6292

Google Scholar
For a review on alkaline earth metal catalysts for asymmetric reactions, see:
1l Kobayashi S. Yamashita Y. Acc. Chem. Res. 2011, 44: 58

Google Scholar
2a Sell MS. Rieke RD. Synth. Commun. 1995, 25: 4107

Google Scholar
For reviews, see:
2b Rieke RD. Sell MS. Klein WR. Chen T.-A. Brown JD. Hanson MV. In Active Metals. Preparation, Characterization, Applications Fürstner A. VCH; Weinheim: 1996. p.1

Google Scholar
2c Rieke RD. Hanson MV. Tetrahedron 1997, 53: 1925

Google Scholar
3 Yanagisawa A. Okitsu S. Arai T. Synlett 2005, 1679

Google Scholar
4 Yanagisawa A. Suzuki T. Koide T. Okitsu S. Arai T. Chem. Asian J. 2008, 3: 1793

Google Scholar
5 Yanagisawa A. Koide T. Yoshida K. Synlett 2010, 1515

Google Scholar
6 Yanagisawa A. Takahashi H. Arai T. Chem. Commun. (Cambridge) 2004, 580

Google Scholar
7 Yanagisawa A. Shinohara A. Takahashi H. Arai T. Synlett 2007, 141

Google Scholar
8 Takahashi H. Arai T. Yanagisawa A. Synlett 2006, 2833

Google Scholar
9 Yanagisawa A. Takahashi H. Arai T. Tetrahedron 2007, 63: 8581

Google Scholar
10 Kazmaier U. Angew. Chem. Int. Ed. 2009, 48: 5790

Google Scholar
11 Kobayashi S. Matsubara R. Chem. Eur. J. 2009, 15: 10694

Google Scholar
12 Yamada YMA. Shibasaki M. Tetrahedron Lett. 1998, 39: 5561

Google Scholar
13 Saito S. Kobayashi S. J. Am. Chem. Soc. 2006, 128: 8704

Google Scholar
14 Yamaguchi A. Matsunaga S. Shibasaki M. J. Am. Chem. Soc. 2009, 131: 10842

Google Scholar
15 Saito S. Tsubogo T. Kobayashi S. Chem. Commun. (Cambridge) 2007, 1236

Google Scholar
16 Yamaguchi A. Aoyama N. Matsunaga S. Shibasaki M. Org. Lett. 2007, 9: 3387

Google Scholar
17 Tsubogo T. Kano Y. Yamashita Y. Kobayashi S. Chem. Asian J. 2010, 5: 1974

Google Scholar
18 Yamatsugu K. Yin L. Kamijo S. Kimura Y. Kanai M. Shibasaki M. Angew. Chem. Int. Ed. 2009, 48: 1070

Google Scholar
19a Epsztein R. In Comprehensive Carbanion Chemistry Buncel E. Durst T. Elsevier; New York: 1984. Chap. 3. p.107

Google Scholar
19b Yamamoto H. In Comprehensive Organic Synthesis Vol. 2: Trost BM. Fleming I. Heathcock CH. Pergamon; Oxford: 1991. p.81

Google Scholar
20a Marshall JA. Chem. Rev. 1996, 96: 31

Google Scholar
20b Marshall JA. Chem. Rev. 2000, 100: 3163

Google Scholar
20c Denmark SE. Fu J. Chem. Rev. 2003, 103: 2763

Google Scholar
20d Ferreira F. Denichoux A. Chemla F. Bejjani J. Synlett 2004, 2051

Google Scholar
20e Marshall JA. J. Org. Chem. 2007, 72: 8153

Google Scholar
21 Yanagisawa A. Habaue S. Yamamoto H. J. Org. Chem. 1989, 54: 5198

Google Scholar
22 Yanagisawa A. Habaue S. Yamamoto H. Tetrahedron 1992, 48: 1969

Google Scholar
23 Kleinman EF. Volkmann RA. In Comprehensive Organic Synthesis Vol. 2: Trost BM. Fleming I. Heathcock CH. Pergamon; Oxford: 1991. p.975

Google Scholar
24a An DK. Hirakawa K. Okamoto S. Sato F. Tetrahedron Lett. 1999, 40: 3737

Google Scholar
24b Waser J. González-Gómez JC. Nambu H. Huber P. Carreira EM. Org. Lett. 2005, 7: 4249

Google Scholar
25a Fürstner A. Synthesis 1989, 571

Google Scholar
25b Rathke MW. Weipert P. In Comprehensive Organic Synthesis Vol. 2: Trost BM. Fleming I. Heathcock CH. Pergamon; Oxford: 1991. p.277

Google Scholar
25c Fürstner A. In Organozinc Reagents Knochel P. Jones P. Oxford University Press; New York: 1999. p.287

Google Scholar
26a Greeves N. In Comprehensive Organic Synthesis Vol. 8: Trost BM. Fleming I. Pergamon; Oxford: 1991. p.1

Google Scholar
26b Gawley RE. Zhang X. In Encyclopedia of Reagents for Organic Synthesis Vol. 6: Paquette LA. John Wiley & Sons; Chichester: 1995. p.4238

Google Scholar
26c Gawley RE. In Encyclopedia of Reagents for Organic Synthesis Vol. 7: Paquette LA. John Wiley & Sons; Chichester: 1995. p.4568

Google Scholar
For typical examples, see:
27a Gnaneshwar R. Wadgaonkar PP. Sivaram S. Tetrahedron Lett. 2003, 44: 6047

Google Scholar
27b Miura K. Nakagawa T. Hosomi A. Synlett 2003, 2068

Google Scholar
27c Nakagawa T. Fujisawa H. Nagata Y. Mukaiyama T. Bull. Chem. Soc. Jpn. 2005, 78: 236

Google Scholar
28a Heathcock CH. In Comprehensive Organic Synthesis Vol. 2: Trost BM. Fleming I. Heathcock CH. Pergamon; Oxford: 1991. p.133

Google Scholar
28b Jung ME. In Comprehensive Organic Synthesis Vol. 4: Trost BM. Fleming I. Semmelhack MF. Pergamon; Oxford: 1991. p.1

Google Scholar
29 Modern Aldol Reactions Vols. 1 and 2: Mahrwald R. Wiley-VCH; Weinheim: 2004.

Google Scholar
30 Geary LM. Hultin PG. Tetrahedron: Asymmetry 2009, 20: 131

Google Scholar
31 Steinreiber J. Faber K. Griengl H. Chem. Eur. J. 2008, 14: 8060

Google Scholar
32a Kobayashi S. Ishitani H. Chem. Rev. 1999, 99: 1069

Google Scholar
32b Córdova A. Acc. Chem. Res. 2004, 37: 102

Google Scholar
32c Friestad GK. Mathies AK. Tetrahedron 2007, 63: 2541

Google Scholar
33a Jensen KB. Thorhauge J. Hazell RG. Jørgensen KA. Angew. Chem. Int. Ed. 2001, 40: 160

Google Scholar
33b Evans DA. Scheidt KA. Fandrick KR. Lam HW. Wu J. J. Am. Chem. Soc. 2003, 125: 10780

Google Scholar
33c Bandini M. Fagioli M. Melchiorre P. Melloni A. Umani-Ronchi A. Tetrahedron Lett. 2003, 44: 5843

Google Scholar
33d Palomo C. Oiarbide M. Kardak BG. García JM. Linden A. J. Am. Chem. Soc. 2005, 127: 4154

Google Scholar
33e Evans DA. Fandrick KR. Song H.-J. J. Am. Chem. Soc. 2005, 127: 8942

Google Scholar
33f Yang H. Hong Y.-T. Kim S. Org. Lett. 2007, 9: 2281

Google Scholar
33g Blay G. Fernández I. Pedro JR. Vila C. Org. Lett. 2007, 9: 2601

Google Scholar
33h Desimoni G. Faita G. Toscanini M. Boiocchi M. Chem. Eur. J. 2008, 14: 3630

Google Scholar
33i Singh PK. Singh VK. Org. Lett. 2008, 10: 4121

Google Scholar
33j Boersma AJ. Feringa BL. Roelfes G. Angew. Chem. Int. Ed. 2009, 48: 3346

Google Scholar
33k Wang W. Liu X. Cao W. Wang J. Lin L. Feng X. Chem. Eur. J. 2010, 16: 1664

Google Scholar
34a Zhou W. Xu L.-W. Li L. Yang L. Xia C.-G. Eur. J. Org. Chem. 2006, 5225

Google Scholar
34b Chen W. Du W. Yue L. Li R. Wu Y. Ding L.-S. Chen Y.-C. Org. Biomol. Chem. 2007, 5: 816

Google Scholar
34c Bartoli G. Bosco M. Carlone A. Pesciaioli F. Sambri L. Melchiorre P. Org. Lett. 2007, 9: 1403

Google Scholar
34d Tang H.-Y. Lu A.-D. Zhou Z.-H. Zhao G.-F. He L.-N. Tag C.-C. Eur. J. Org. Chem. 2008, 1406

Google Scholar
34e Rueping M. Nachtsheim BJ. Moreth SA. Bolte M. Angew. Chem. Int. Ed. 2008, 47: 593

Google Scholar
35 Corey EJ. Angew. Chem. Int. Ed. 2002, 41: 1650

Google Scholar