ASYMMETRIC INDUCTION IN THE DIELS-ALDER REACTION USING CHIRAL METALLOCENE CATALYSTS

被引：66
作者：
HONG, YP [1 ]
KUNTZ, BA [1 ]
COLLINS, S [1 ]
机构：
[1] UNIV WATERLOO, DEPT CHEM, WATERLOO N2L 3G1, ONTARIO, CANADA
来源：
ORGANOMETALLICS | 1993年 / 12卷 / 03期
关键词：
D O I：
10.1021/om00027a056
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The Diels-Alder reaction between cyclopentadiene and various dienophiles is efficiently catalyzed by cationic zirconocene compounds (e.g. [Cp2Zr(OtBu)-THF][BPh4] (2)). The use of catalytic amounts of optically pure (S)-[ethylenebis(eta5-tetrahydroindenyl)]-zirconium tert-butoxide tetrahydrofuran tetraphenylborate (3) resulted in modest enantioselectivity in this C-C bond-forming process. Compound (S)-3 crystallizes in the hexagonal space group P6(1): a = 11.607(2) angstrom, c = 55.363(9) angstrom, V = 6459(2) angstrom3, Z = 6 with R = 0.0278, R(w) = 0.0273 for 2534 observed reflections with F > 6.0 sigma(F). A model for the facial selectivity observed is presented on the basis of the structure of compound (S)-3.
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页码：964 / 969
页数：6
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