An Efficient Stereoselective Synthesis of Substituted 1,3-Dienes

Kyungsoo Oh; Philip J. Parsons; Dave Cheshire

doi:10.1055/s-2004-836022

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Synlett 2004(15): 2771-2775
DOI: 10.1055/s-2004-836022

LETTER

An Efficient Stereoselective Synthesis of Substituted 1,3-Dienes

Kyungsoo Oh^a,, Philip J. Parsons*^a, Dave Cheshire^b
^a Department of Chemistry, University of Sussex, Falmer, Brighton BN1 9QJ, UK
^b Department of Medicinal Chemistry, AstraZeneca Pharmaceuticals, Bakewell Road, Loughborough LE11 5RH, UK
Fax: +44(1273)677196; e-Mail: P.J.Parsons@sussex.ac.uk;

Further Information

Publication History

Received 13 August 2004
Publication Date:
12 November 2004 (online)

Abstract
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Abstract

A stereoselective synthesis of substituted 1,3-dienes has been developed which utilises an Ireland-Claisen rearrangement/silicon-mediated fragmentation sequence. This sequence has been designed to introduce remote centres of asymmetry as well as stereodefined diene systems, and its application to an aziridine system is also described.

Key words

aziridine - Ireland-Claisen rearrangement - Sharpless asymmetric epoxidation - silicon-mediated fragmentation

References

2 Trost BM. Pinkerton AB. Seidel M. J. Am. Chem. Soc. 2001, 123: 12466

Crossref Google Scholar
3 Oppolzer W. In Comprehensive Organic Synthesis Vol. 5: Trost BM. Fleming I. Pergamon; Oxford: 1991.

Google Scholar
4a Ojima I. Tzamarioudaki M. Li Z. Donovan RJ. Chem. Rev. 1996, 96: 635

Google Scholar
4b Lautens M. Klute W. Tam W. Chem. Rev. 1996, 96: 49

Google Scholar
5a Corey EJ. Angew. Chem. Int. Ed. 2002, 41: 1650

Crossref PubMed Google Scholar
5b Nicolaou KC. Snyder SA. Montagon T. Vassilikogiannakis GE. Angew. Chem. Int. Ed. 2002, 41: 1668

Crossref PubMed Google Scholar
6a Eshelby J. Parsons PJ. Crowley PJ. J. Chem. Soc., Chem. Commun. 1995, 1497

Crossref Google Scholar
6b Hiscock SD. Hitchcock PB. Parsons PJ. Tetrahedron 1998, 54: 11567

Crossref Google Scholar
7a Hanson RM. Sharpless KB. J. Org. Chem. 1986, 51: 1922

Google Scholar
7b Gao Y. Hanson RM. Klunder JM. Ko SY. Masamune H. Sharpless KB. J. Am. Chem. Soc. 1987, 108: 5765

Google Scholar
8 Mancus AJ. Huang SL. Swern D. J. Org. Chem. 1978, 43: 2480

Crossref Google Scholar
9 Parikh JR. von Doering WE. J. Am. Chem. Soc. 1967, 89: 5505

Crossref Google Scholar
10a Schlosser M. Wei H. Tetrahedron 1997, 53: 1735

Crossref Google Scholar
10b Godebout V. Lecomte S. Levasseur F. Duharrel L. Tetrahedron Lett. 1996, 37: 7255

Crossref Google Scholar
10c Klinguer C. Melnyk O. Loing E. Gras-Masse H. Tetrahedron Lett. 1996, 37: 7259

Crossref Google Scholar
10d Urabe H. Matsuka T. Sato F. Tetrahedron Lett. 1992, 33: 4179

Crossref Google Scholar
11a Escudier JM. Baltas M. Gorrichon L. Tetrahedron Lett. 1991, 32: 5345

Crossref Google Scholar
11b Escudier JM. Baltas M. Gorrichon L. Tetrahedron Lett. 1991, 32: 5253

Crossref Google Scholar
11c Howe GP. Wang S. Procter G. Tetrahedron Lett. 1987, 28: 2629

Crossref Google Scholar
12a Ireland RE. Wipf P. Xiang J. J. Org. Chem. 1991, 56: 3572

Crossref Google Scholar
12b Ireland RE. Wipf P. Armstrong JD. J. Org. Chem. 1991, 56: 650

Crossref Google Scholar
14 Crandall JK. Aprru M. Org. React. 1983, 29: 345 ; see Scheme 4

Google Scholar
15a Miller JF. Termin A. Koch K. Piscopio AD. J. Org. Chem. 1998, 63: 3158

Google Scholar
15b Panek JS. Clark TD. J. Org. Chem. 1992, 57: 4323

Google Scholar
15c Sparks MA. Panek JS. J. Org. Chem. 1991, 56: 3431

Google Scholar
15d Burke S. Fpbare WF. Pacofsky GJ. J. Org. Chem. 1983, 48: 5221

Google Scholar
18a Ziegler FE. Belema M. J. Org. Chem. 1994, 59: 7962

Google Scholar
18b Wipf P. Fritch PC. J. Org. Chem. 1994, 59: 4875

Google Scholar
18c Legters J. Thijs L. Zwanenburg B. Recl. Trav. Chim. Pays-Bas 1992, 111: 1

Google Scholar
18d Legters J. Thijs L. Zwanenburg B. Recl. Trav. Chim. Pays-Bas 1992, 111: 16

Google Scholar
20 Cardillo G. Gentilucci L. Tolomelli A. Tomasini C. J. Org. Chem. 1998, 63: 3458

Crossref Google Scholar

1

New address: Kyungsoo Oh, Department of Chemistry, University of Pennsylvania, 231S, 34th Street, Philadelphia, PA 19104, USA.

13

A single crystal of 6a of 3,5-dinitrobenzoyl derivative was obtained and the selectivity of 5b and 6b were made from analogy of our Galbonolide study.

16

Stereoselective epoxide opening using Ti(i-PrO)₄ (Scheme [5] ).

17

BF₃·OEt₂ initiated fragmentation of 9a followed by dehydration of 10a to give 9d (Scheme [6] ).

19

Aziridine opening by chloride anion in esterification conditions (Scheme [7] ).

21

Conditions using LHMDS and TMSCl-Et₃N did not yield any identifiable product.