A NOVEL REARRANGEMENT OF OXAZOLIDIN-2-THIONE CHIRAL AUXILIARIES IN THE PREPARATION OF ALPHA-ALKYL-BETA-HYDROXY ESTERS

被引：0

作者：

ADAMCZYK, M

MATTINGLY, PG

PAN, Y

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来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 30期

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中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aldol condensation of serine-derived N-acyl-3-carbomethoxyoxazolidin-2-thiones via the boron enolate gave the syn aldol products in high enantiomeric excess. Methanolysis to the alpha-alkyl-beta-hydroxy methyl esters proceeded in unexpectedly low yield. Rearrangement of the aldol product to the tetrahydro 3-(3-hydroxy-2-carbomethoxypropyl)-2-thioxo-4H-1,3-oxazin-4-one was observed on storage or treatment with base.

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页码：5303 / 5306

页数：4

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