Enantioselective synthesis of both enantiomers of 3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone

被引：17

作者：

Camps, P ^{[1
]}

Pérez, F ^{[1
]}

Soldevilla, N ^{[1
]}

机构：

[1] Univ Barcelona, Fac Farm, Quim Farmaceut Lab, E-08028 Barcelona, Spain

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 37期

关键词：

asymmetric synthesis; hydrogenation; reduction; hydroxy acids and derivatives;

D O I：

10.1016/S0040-4039(99)01383-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral auxiliaries (R)- and (S)-3-Hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidi none were obtained in good yield and e.e. by enantioselective reduction of 4,4-dimethyl-1-phenylpyrrolidine-2,3-dione with (-)- and (+)-B-chlorodiisopinocamphenylborane, (-)- and (+)-DIP-Chloride(R), respectively. The (R)-enantiomer was also obtained by enantioselective hydrogenation of the same precursor using a complex of 1,5-cyclooctadiene Rh(I) and (2S,4S)-1-(tert-butoxycarbonyl)-4-(diphenylphosphino)-2-(diphenylphosphinomethyl)pyrrolidine,(S,S)-BPPM, as the chiral catalyst. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：6853 / 6856

页数：4

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