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Synlett 2018; 29(19): 2456-2460
DOI: 10.1055/s-0037-1610552
DOI: 10.1055/s-0037-1610552
synpacts
Facile Access to Cyclopentadienes via Catalytic Intramolecular Palladium-Ene Reaction of 2,4-Pentadienyl Acetates
IISER Mohali is acknowledged for funding and for providing the infrastructure. S.K.B (first author) thanks IASc-INSA-NASI FAST-SF 2018. S.K.B. (second author) thanks IISER Mohali for a fellowship.Weitere Informationen
Publikationsverlauf
Received: 15. Juni 2018
Accepted: 10. Juli 2018
Publikationsdatum:
02. August 2018 (online)
![](https://www.thieme-connect.de/media/synlett/201819/lookinside/thumbnails/st-2018-p0369-sp_10-1055_s-0037-1610552-1.jpg)
Abstract
We have recently disclosed a palladium-catalyzed Trost–Oppolzer type Alder-ene reaction of 2,4-pentadienyl acetates for the synthesis of highly substituted cyclopentadienes and cyclopentene-fused aromatics. The overall transformation also represents an acid-free iso-Nazarov type cyclization. Herein, we provide the hypothesis and rationale behind this work, while highlighting the seminal contributions of Trost, Oppolzer and others towards the development of the palladium-ene reaction.
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References
- 1a Tsuji J. Takahashi H. Morikawa M. Tetrahedron Lett. 1965; 6: 4387
- 1b Trost BM. Fullerton TJ. J. Am. Chem. Soc. 1973; 95: 292
- 1c Trost BM. Weber L. Strege PE. Fullerton TJ. Diestche TJ. J. Am. Chem. Soc. 1978; 100: 3416
- 1d Trost BM. Angew. Chem. Int. Ed. Engl. 1989; 28: 1173
- 2a Trost BM. Acc. Chem. Res. 1996; 29: 355
- 2b Jellerichs G. Kong J.-R. Krische MJ. J. Am. Chem. Soc. 2003; 125: 7758
- 2c Kazmaier U. Curr. Org. Chem. 2003; 7: 317
- 2d Miyabe H. Takemoto Y. Synlett 2005; 1641
- 2e You S.-L. Dai L.-X. Angew. Chem. Int. Ed. 2006; 45: 5246
- 2f Braun M. Meier T. Angew. Chem. Int. Ed. 2006; 45: 6952
- 2g Ibrahem I. Còrdova A. Angew. Chem. Int. Ed. 2006; 45: 1952
- 2h Lu Z. Ma S. Angew. Chem. Int. Ed. 2008; 47: 258
- 2i Jensen T. Fristrup P. Chem. Eur. J. 2009; 15: 9632
- 2j Weaver JD. Recio III A. Grenning AJ. Tunge JA. Chem. Rev. 2011; 111: 1846
- 2k Kammerer C. Prestat G. Madec D. Poli G. Acc. Chem. Res. 2014; 47: 3439
- 2l Liu Y. Han S.-J. Liu W.-B. Stoltz BM. Acc. Chem. Res. 2015; 48: 740
-
2m
Trost BM.
Tetrahedron 2015; 71: 5708
- 3a Trost BM. Hung M.-H. J. Am. Chem. Soc. 1984; 106: 6837
- 3b Andersson PG. Backvall J.-E. J. Org. Chem. 1991; 56: 5349
- 3c Nilsson YI. M. Andersson PG. Backvall J.-E. J. Am. Chem. Soc. 1993; 115: 6609
- 3d Kang S.-K. Park D.-C. Jeon J.-H. Rho H.-S. Yu C.-M. Tetrahedron Lett. 1994; 35: 2357
- 3e Trost BM. Bunt RC. J. Am. Chem. Soc. 1998; 120: 70
- 3f Shimizu I. Matsumoto Y. Nishikawa M. Kawahara T. Satake A. Yamamoto A. Chem. Lett. 1998; 27: 983
- 3g Schobert R. Barnickel B. Synthesis 2009; 2778
- 4 Brummond KM. Loyer-Drew JA. C–C Bond Formation (Part 1) by Addition Reactions: Alder-Ene Reaction . In Comprehensive Organometallic Chemistry III, Vol. 10. Crabtree RH. Mingos MP. Ojima I. Elsevier; Oxford: 2007. Chap. 10.12
- 5a Oppolzer W. Pitteloud R. Strauss HF. J. Am. Chem. Soc. 1982; 104: 6476
- 5b Trost BM. Lautens M. J. Am. Chem. Soc. 1985; 107: 1781
- 5c Oppolzer W. Gaudin J.-M. Birkinshaw TN. Tetrahedron Lett. 1988; 29: 4705
- 5d Oppolzer W. Keller TH. Bedoya-Zurita M. Stone C. Tetrahedron Lett. 1989; 30: 5883
- 5e Takacs JM. Newsome PW. Kuehn C. Tetrahedron 1990; 46: 5507
- 5f Oppolzer W. Pure Appl. Chem. 1990; 62: 1941
- 5g Oppolzer W. Furstner A. Helv. Chim. Acta 1993; 76: 2329
- 5h Meyer C. Marek I. Courtemanche G. Normant J.-F. J. Org. Chem. 1995; 60: 863
- 5i Llerena D. Aubert C. Malacria M. Tetrahedron Lett. 1996; 37: 7027
- 5j Trost BM. Toste FD. Tetrahedron Lett. 1999; 40: 7739
- 5k Trost BM. Machacek RM. Schnaderbeck MJ. Org. Lett. 2000; 2: 1761
- 5l Kel’in AV. Sromek AW. Gevorgyan V. J. Am. Chem. Soc. 2001; 123: 2074
- 5m Brummond KM. Chen H. Sill P. You L. J. Am. Chem. Soc. 2002; 124: 15186
- 5n Trost BM. Machacek RM. Ball ZT. Org. Lett. 2003; 5: 1895
- 5o Hilt G. Treutwein J. Angew. Chem. Int. Ed. 2007; 46: 8500
- 5p Schwier T. Sromek AW. Yap DM. L. Chemyak D. Gevorgyan V. J. Am. Chem. Soc. 2007; 129: 9868
- 5q Fürstner A. Majima K. Martin R. Krause H. Kattnig F. Goddard R. Lehmann CW. J. Am. Chem. Soc. 2008; 130: 1992
- 5r Fukamizu K. Miyake Y. Nishibayashi Y. J. Am. Chem. Soc. 2008; 130: 10498
- 6a Trost BM. Krische M. J. J. Am. Chem. Soc. 1996; 118: 233
- 6b Pearson AJ. Wang X. J. Am. Chem. Soc. 2003; 125: 13326
- 6c Roethle PA. Trauner D. Org. Lett. 2006; 8: 345
- 6d Watson ID. G. Toste FD. Chem. Sci. 2012; 3: 2899
- 6e Marinetti A. Jullien H. Voituriez A. Chem. Soc. Rev. 2012; 41: 4884
- 6f Crisp AL. Li J. Lan P. Nugent J. Matousova E. Banwell MG. Aust. J. Chem. 2015; 68: 1183
- 7 Bankar SK. Singh B. Tung P. Ramasastry SS. V. Angew. Chem. Int. Ed. 2018; 57: 1678
- 8a Halterman RL. Chem. Rev. 1992; 92: 965
- 8b Kotora M. Top. Organomet. Chem. 2004; 8: 57
- 8c Enders M. Baker RW. Curr. Org. Chem. 2006; 10: 937
- 8d Ye B. Cramer N. Acc. Chem. Res. 2015; 48: 1308
- 8e Coombs JR. Morken JP. Angew. Chem. Int. Ed. 2016; 55: 2636
- 9a Bee C. Leclerc E. Tius MA. Org. Lett. 2003; 5: 4927
- 9b Basak AK. Shimada N. Bow WF. Vicic DA. Tius MA. J. Am. Chem. Soc. 2010; 132: 8266
- 9c Cai Z.-X. Harmata M. Org. Lett. 2010; 12: 5668
- 9d Subramanium SS. Handa S. Miranda AJ. Slaughter LM. ACS Catal. 2011; 1: 1371
- 9e Kitamura K. Shimada N. Stewart C. Atesin AC. Atesin TA. Tius MA. Angew. Chem. Int. Ed. 2015; 54: 6288
- 9f Riveira MJ. Marsili LA. Mischne MP. Org. Biomol. Chem. 2017; 15: 9255
- 10a Funami H. Kusama H. Iwasawa N. Angew. Chem. Int. Ed. 2007; 46: 909
- 10b Lee JH. Toste FD. Angew. Chem. Int. Ed. 2007; 46: 912
- 11 Sarnpitak P. Trongchit K. Kostenko Y. Sathalalai S. Gleeson MP. Ruchirawat S. Ploypradith P. J. Org. Chem. 2013; 78: 8281
- 12a Majetich G. Shimkus JM. J. Nat. Prod. 2010; 73: 284
- 12b Gabriele B. Mancuso R. Veltri L. Chem. Eur. J. 2016; 22: 5056
- 12c Chanda T. Singh MS. Org. Biomol. Chem. 2016; 14: 8895
- 13a Baraznenok IL. Nenajdenko VG. Balenkova ES. Synthesis 1997; 465
- 13b Somei M. Yamada F. Nat. Prod. Rep. 2005; 22: 73
- 13c Cacchi S. Fabrizi G. Chem. Rev. 2005; 105: 2873
- 13d Higuchi K. Kawasaki T. Nat. Prod. Rep. 2007; 24: 843
- 13e Kochanowska-Karamyan AJ. Hamann MT. Chem. Rev. 2010; 110: 4489
- 13f Ie Y. Nishida K. Karakawa M. Tada H. Aso Y. J. Org. Chem. 2011; 76: 6604
- 14a Snyder SA. Zografos AL. Lin Y. Angew. Chem. Int. Ed. 2007; 46: 8186
- 14b Jeffrey JL. Sarpong R. Org. Lett. 2009; 11: 5450
- 14c Snyder SA. Breazzano SP. Ross AG. Lin Y. Zografos AL. J. Am. Chem. Soc. 2009; 131: 1753
- 14d Kim H. Nagaki A. Yoshida J.-I. Nat. Chem. 2011; 2: 264
- 14e Lee BH. Choi YL. Shin S. Heo J.-N. J. Org. Chem. 2011; 76: 6611
- 14f Yang Y. Philips D. Pan S. J. Org. Chem. 2011; 76: 1902
- 14g Kerr DJ. Miletic M. Manchala N. White JM. Flynn BL. Org. Lett. 2013; 15: 4118
- 14h Du B. Jiang X. Sun P. J. Org. Chem. 2013; 78: 2786