Stereocontrolled ring-opening of some enantiomerically enriched epoxy ketones and epoxy alcohols using trimethylaluminium:: synthesis of (S)-2-arylpropanoic acids

被引：34

作者：

Carde, L

Davies, DH

Roberts, SM

机构：

[1] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England

[2] AstraZeneca, Macclesfield SK10 4TG, Cheshire, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 15期

关键词：

D O I：

10.1039/b000996m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Poly-(D)-leucine-catalysed epoxidation of chalcone furnished epoxide (+)-6; treatment of this epoxide with trimethylaluminium followed by zinc borohydride reduction and oxidative cleavage furnished (S)-2-phenylpropanoic acid 11. In a complementary sequence epoxy ketones (-)-6 and 25 were converted into (S)-2-phenylpropanoic acid and (S)-fenoprofen 5 respectively by reduction with zinc borohydride, reaction with trimethylaluminium and oxidative cleavage. Similarly epoxy ketones (-)-6, 21 and 28 were treated with methylmagnesium iodide, trimethylaluminium and the resultant alcohols subjected to oxidative cleavage to afford (S)-2-phenylpropanoic acid (from the first two substrates) and (S)-naproxen 1.

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页码：2455 / 2463

页数：9

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