Diastereoselective Ireland-Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins

被引：9

作者：

Davies, Stephen G. ^{[1
]}

Fletcher, Ai M. ^{[1
]}

Lee, James A. ^{[1
]}

Roberts, Paul M. ^{[1
]}

Souleymanou, Myriam Y. ^{[1
]}

Thomson, James E. ^{[1
]}

Zammit, Charlotte M. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 17期

关键词：

PARALLEL KINETIC RESOLUTION; HOMOCHIRAL LITHIUM AMIDES; RING-CLOSING IODOAMINATION; JASPINE-B PACHASTRISSAMINE; D-LYXO-PHYTOSPHINGOSINE; CONJUGATE ADDITION; ALPHA; BETA-UNSATURATED ESTERS; STEREOCHEMICAL CONTROL; STEREOSELECTIVE-SYNTHESIS; AMMONIA EQUIVALENTS;

D O I：

10.1039/c4ob00274a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diastereoselective Ireland-Claisen rearrangement of a range of substituted allyl beta-amino esters gave the corresponding enantiopure alpha-substituted-beta-amino esters with good diastereoselectivity. The application of this methodology in the asymmetric synthesis of a range of C(5)-substituted 1,2-anti-1,5-syn-transpentacins was demonstrated by the rearrangement of a range of beta-amino esters derived from sorbic acid, followed by esterification, ring-closing metathesis, hydrogenolytic deprotection/reduction, and hydrolysis, which gave the C(5)-substituted transpentacins in only 9 steps from commercially available starting materials.

引用

页码：2702 / 2728

页数：27

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