Asymmetric syntheses of dihydroxyhomoprolines via doubly diastereoselective lithium amide conjugate addition reactions

被引：14

作者：

Davies, Stephen G. ^{[1
]}

Foster, Emma M. ^{[1
]}

Lee, James A. ^{[1
]}

Roberts, Paul M. ^{[1
]}

Thomson, James E. ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2013年 / 69卷 / 41期

关键词：

Lithium amide; Conjugate addition; Asymmetric synthesis; Doubly diastereoselective; Homoprolines; PARALLEL KINETIC RESOLUTION; RING-CLOSING IODOAMINATION; JASPINE-B PACHASTRISSAMINE; D-LYXO-PHYTOSPHINGOSINE; BETA-AMINO ESTERS; MICHAEL ADDITION; AMMONIA EQUIVALENTS; TRANS-DIOXOLANE; ACID; PEPTIDES;

D O I：

10.1016/j.tet.2013.07.096

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric syntheses of novel dihydroxyhomoprolines have been achieved using the doubly diastereoselective conjugate additions of the antipodes of lithium N-benzyl-N-(alpha-methylbenzyl)amide to a set of four chiral alpha,beta-unsaturated esters (derived from D-pentoses) as one of the key steps. A full account of the diastereoselectivity observed in these conjugate additions is presented and the stereochemical outcomes of these reactions have been established unambiguously via a combination of hydrogenolytic chemical correlation and single crystal X-ray diffraction analyses. A tandem hydrogenolysis/intramolecular reductive amination reaction was then used to create the corresponding enantiopure pyrrolidines, providing access to (2'S,3'5,4'R)-dihydroxyhomoproline and (2'S,3'R,4'S)-dihydroxyhomoproline after deprotection. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：8680 / 8704

页数：25

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