SOME ENANTIOSELECTIVE BORANE REDUCTIONS OF PROCHIRAL KETONES CATALYZED BY POLYMER-SUPPORTED OXAZABOROLIDINES BOUND VIA THE BORON ATOM

被引：39

作者：

CAZE, C ^{[1
]}

ELMOUALIJ, N ^{[1
]}

HODGE, P ^{[1
]}

LOCK, CJ ^{[1
]}

MA, JB ^{[1
]}

机构：

[1] UNIV MANCHESTER,DEPT CHEM,MANCHESTER M13 9PL,LANCS,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 04期

关键词：

D O I：

10.1039/p19950000345

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Polystyrenes containing arylboronic acid residues were prepared and treated with norephedrine to give polymer-supported (PS) chiral oxazaborolidines. The latter were investigated as catalysts for the reductions of acetophenone and/or propiophenone by the borane-dimethyl sulfide complex. A variety of reaction conditions was used. The results were compared with those obtained using the non-polymeric analogue of the catalysts prepared by reaction of (1R,2S)-(-)norephedrine with phenylboronic acid. When used under the best reaction conditions of those investigated (30 mol% of catalyst in tetrahydrofuran at 20 degrees C) the percentage ees obtained with the better PS catalyst were almost the same as those obtained using the non-polymeric analogue under similar reaction conditions. It was shown that the PS reaction with propiophenone was >95% complete in 20 min. The PS catalyst could be recycled successfully at least three times.

引用

页码：345 / 349

页数：5

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