A simple and efficient synthesis of enantiomeric (3aRS,4RS,6aSR)-4-hydroxy-3,3a,4,6a-tetrahydro-1H-cyclopenta[c]furan-1-ones

被引：16

作者：

Gimazetdinov, Airat M. ^{[1
]}

Gataullin, Salavat S. ^{[1
]}

Bushmarinov, Ivan S. ^{[2
]}

Miftakhov, Mansur S. ^{[1
]}

机构：

[1] Russian Acad Sci, Inst Organ Chem, Ufa Res Ctr, Ufa 450054, Russia

[2] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Moscow 119991, Russia

来源：

TETRAHEDRON | 2012年 / 68卷 / 29期

关键词：

(+)-alpha-Methylbenzylamine; Chiral auxiliary; gamma-Lactones; Cyclopentene block-synthons; Optical resolution; ENANTIOSELECTIVE SYNTHESIS; PROSTAGLANDINS; INTERMEDIATE; ALLYLSILANE;

D O I：

10.1016/j.tet.2012.05.036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereomeric amides produced via the cleavage of easily available (+/-)-7,7-dichloro-4-exo-trimethylsilylbicyclo[3.2.0]hept-2-en-6-one by treatment with (+)-alpha-methylbenzylamine were transformed into bicyclic lactam-aminals, which can easily be separated by column chromatography on SiO2. The latter products lead to enantiomeric (3a,6a)-4-hydroxy-3,3a,4,6a-tetrahydro-1H-cyclopenta[c]furan-1-ones after the removal of the chiral auxiliary and epoxidation. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：5754 / 5758

页数：5

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