SILICON-DIRECTED DIENE SYNTHESIS

被引：27

作者：

BROWN, PA ^{[1
]}

BONNERT, RV ^{[1
]}

JENKINS, PR ^{[1
]}

LAWRENCE, NJ ^{[1
]}

SELIM, MR ^{[1
]}

机构：

[1] UNIV LEICESTER,DEPT CHEM,LEICESTER LE1 7RH,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 08期

关键词：

D O I：

10.1039/p19910001893

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of 2-substituted-1,3-dienes is reported which uses silicon as a control element: Eight aldehydes were converted into alpha-silyl ketones by treatment with trimethylsilylmethylmagnesium chloride and rapid Collins oxidation. Addition of vinylmagnesium bromide to the resulting alpha-silyl ketones, followed by Peterson elimination, gave a series of dienes. The route was used to make (4S)-3-methylene-t-[(phenylmethoxy)methoxy]pent-1-ene from (-)-ethyl lactate; low asymmetric induction was observed in the Diels-Alder reactions of this diene with diethyl fumarate and N-phenylmaleimide.

引用

页码：1893 / 1900

页数：8

共 64 条

[61] SYNTHETIC REACTIONS USING ORGANOTIN AND SULFUR-COMPOUNDS .7. STANNANES IN SYNTHESIS - A NEW ROUTE TO 2-SUBSTITUTED-1,3-BUTADIENES VIA STEREOSELECTIVE ALLYLTIN FORMATION UNDER HOMOLYTIC CONDITIONS [J].