Stereoselective oxazaborolidine-borane reduction of biphenyl alkyl diketones-lignin models: enantiopure dehydrodiapocynol derivatives

被引：17

作者：

Delogu, G

Dettori, MA

Patti, A

Pedotti, S

Forni, A

Casalone, G

机构：

[1] CNR, Ist Chim Biomol, Sez Sassari, I-07040 Sassari, Italy

[2] CNR, Ist Chim Biomol, Sez Catania, I-95028 Valverde, CT, Italy

[3] CNR, Ist Sci & Tecnol Mol, I-20133 Milan, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 16期

关键词：

D O I：

10.1016/S0957-4166(03)00449-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Asymmetric reduction of two conformationally flexible biphenyl alkyl diketones 9 and 10 with (R)-oxazaborolidine 3-borane system was Successfully carried out and the corresponding biphenyl alcohols 11 and 12 were obtained in high yield and e.e. with predominance of the homochiral (S,S) dicarbinols. The absolute configuration of diastereopure dehydrodiapocynol derivative (S.S)-14 was assigned by crystallographic analysis which confirms the known stereochemical course of CBS-catalysed reduction of ketones and gives useful information on spatial arrangement. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：2467 / 2474

页数：8

共 82 条

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