C2-symmetric bis-thioglycosides as new ligands for palladium-catalyzed allylic substitutions

被引：34

作者：

Khiar, N

Araújo, CS

Alvarez, E

Fernández, I

机构：

[1] Univ Seville, CSIC, Inst Invest Quim, Seville 41092, Spain

[2] Univ Seville, Fac Farm, Dept Quim Organ & Farmaceut, E-41012 Seville, Spain

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 16期

关键词：

C-2-symmetric bis-thioglycosides; asymmetric catalysis; ligand design; parallel synthesis; carbohydrates;

D O I：

10.1016/S0040-4039(03)00568-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new divergent design for the synthesis of optically pure bis-thioglycoside type I is reported. In only two steps a common chiral intermediate with up to eight free alcohols: two primary and six secondary is obtained. From this common intermediate a large number of ligands can be synthesized. A positional scanning like strategy has permitted the rapid discovery of an efficient catalyst for the palladium-catalyzed asymmetric allylation of malonate. Dynamic NMR spectroscopy of a Pd(II) complex has shown that there is an efficient stereochemical control of the sulfur configuration upon coordination to the palladium. (C) 2003 Elsevier Science Ltd. All rights reserved.

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页码：3401 / 3404

页数：4

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