Enantiocontrol in the [2,3]-Wittig-rearrangement

被引：10

作者：

Barrett, IM ^{[1
]}

Breeden, SW ^{[1
]}

机构：

[1] Natl Univ Ireland, Dept Chem, Galway, Ireland

来源：

TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 19期

关键词：

D O I：

10.1016/j.tetasy.2004.08.014

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The enantioselective [2,3]-Wittig rearrangement of benzyl prenyl ether has been studied. Treatment of this ether with butyl lithium bearing diamines or bis(oxazoline)s as external chiral ligands (ECL) gave the expected alcohol in up to 66% ee, the highest reported for this transformation. The optimum ECL is based on the bis(oxazoline) system and the C5 substituent on the bis(oxazoline) is crucial to determining both the degree and sense of asymmetric induction. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：3015 / 3017

页数：3

共 21 条

[1] Highly enantioselective chiral base mediated [2,3]-Wittig rearrangement
Gibson, SE
Ham, P
Jefferson, GR
[J]. CHEMICAL COMMUNICATIONS, 1998, (01) : 123 - 124
[2] Hoppe D, 1997, ANGEW CHEM INT EDIT, V36, P2283
[3] ASYMMETRIC-SYNTHESIS OF 1,1-DISUBSTITUTED TETRALINS AND DIHYDRONAPHTHALENES BY DIASTEREOSELECTIVE ADDITION OF LITHIOSILANES TO CHIRAL NAPHTHALENES
HULME, AN
MEYERS, AI
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (05) : 952 - 953
[4] Kawasaki T, 1998, SYNLETT, P1429
[5] Enantio selective carboxylation of α-methoxybenzyllithium generated via asymmetric lithiation with a t-BuLi/chiral bis(oxazoline) complex
Komine, N
Wang, LF
Tomooka, K
Nakai, T
[J]. TETRAHEDRON LETTERS, 1999, 40 (37) : 6809 - 6812
[6] Manabe S, 1998, CHEM PHARM BULL, V46, P335
[7] Enantioselective [2,3] sigmatropic rearrangement mediated by a butyllithium-chiral ligand complex
Manabe, S
[J]. CHEMICAL COMMUNICATIONS, 1997, (08) : 737 - 738
[8] ENANTIOSELECTIVE SYNTHESIS OF MACROCYCLIC PROPARGYLIC ALCOHOLS BY [2,3] WITTIG RING CONTRACTION - SYNTHESIS OF (+)-ARISTOLACTONE AND CEMBRANOID PRECURSORS
MARSHALL, JA
LEBRETON, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (09) : 2925 - 2931
[9] MARSHLL JA, 1991, SELECTIVE COMPREHENS, P975
[10] [2,3]-WITTIG SIGMATROPIC REARRANGEMENTS IN ORGANIC-SYNTHESIS
NAKAI, T
MIKAMI, K
[J]. CHEMICAL REVIEWS, 1986, 86 (05) : 885 - 902

← 1 2 3 →