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：15
|
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
收藏
页码：5754 / 5758
页数：5
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