Synthesis of isoaminile mediated by enzymes

被引：11

作者：

Antonietti, F ^{[1
]}

Brenna, E ^{[1
]}

Fuganti, C ^{[1
]}

Gatti, FG ^{[1
]}

Giovenzana, T ^{[1
]}

Grande, V ^{[1
]}

Malpezzi, L ^{[1
]}

机构：

[1] Ctr CNR Chim Sostanze Nat, Dipartimento Chim Mat & Ingn Chim G Natta Politec, I-20131 Milan, Italy

来源：

SYNTHESIS-STUTTGART | 2005年 / 07期

关键词：

drugs; enzymes; enantiomeric resolutions; rearrangements; lactones;

D O I：

10.1055/s-2005-861856

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A lipase-mediated synthesis of all four enantiomers of isoaminile is reported. The key issues of the paper are: (i) enantioselective acetylation of allylic alcohol (E)-(+/-)-5 to give (E,S)-5 (ee = 92%) and (E,R)-6 (ee > 99%); (ii) Claisen-Johnson rearrangement of R and S enantiomers of 5 to generate the quaternary benzylic stereocenter; (iii) chromatographic separation of aldehyde diastereoisomers; (iv) X-ray structure of aldehyde (2R,4R)-10; (v) unpredicted formation of lactone 12 during the hydrolysis of 11.

引用

收藏

页码：1148 / 1156

页数：9

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