Asymmetric hetero Diels-Alder reaction catalyzed by chiral cationic palladium(II) and platinum(II) complexes

被引：83

作者：

Oi, S ^{[1
]}

Terada, E ^{[1
]}

Ohuchi, K ^{[1
]}

Kato, T ^{[1
]}

Tachibana, Y ^{[1
]}

Inoue, Y ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Engn, Dept Chem Mat, Sendai, Miyagi 9808579, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 23期

关键词：

D O I：

10.1021/jo9906680

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hetero Diels-Alder reaction of nonactivated conjugated dienes 1 with arylglyoxals 2 and glyoxylate esters 7 proceeded enantioselectively in the presence of a catalytic amount of cationic chiral BINAP-palladium or -platinum complexes and 3 Angstrom molecular sieves (MS3A). The addition of MS3A effectively improved the enantioselectivity of the reaction. Excellent ee's were obtained from the reactions of 2,3-dimethyl-1,3-butadiene (1a) and 1,3-cyclohexadiene (1d) with dienophiles 2 and 7. The square-planar structure of [Pd(S-BINAP)(PhCN)(2)](PF6)(2) was determined by X-ray diffraction, and a chiral induction model involving the square-planar palladium complex coordinated with BINAP and a dienophile is proposed.

引用

页码：8660 / 8667

页数：8

共 46 条

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