Understanding the correlation of structure and selectivity in the chiral-phosphoramide-catalyzed enantioselective allylation reactions:: Solution and solid-state structural studies of bisphosphoramide•SnCl4 complexes

被引：93

作者：

Denmark, SE ^{[1
]}

Fu, JP ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 08期

关键词：

D O I：

10.1021/ja021280g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Complexation of bisphosphoramides, linked by various length methylene tethers, with tin tetrachloride was studied by both solution NMR spectroscopy and single-crystal X-ray crystallography. The formation of cis-configured, octahedral 1/1 bisphosphoramide.SnCl4 complexes was supported by both crystallographic and solution NMR studies. In addition, the formation of such complexes was shown to be highly dependent on the tether length and solution concentration. Single-crystal X-ray analysis of bisphosphoramide.SnCl4 complexes also provided detailed information on the stereochemical environment relevant to the enantioselectivity of asymmetric allylation reactions.

引用

页码：2208 / 2216

页数：9

共 51 条

[1] Angell RM, 1997, CHEM COMMUN, P919
[2] TRANS-INFLUENCE - ITS MEASUREMENT AND SIGNIFICANCE
APPLETON, TG
CLARK, HC
MANZER, LE
[J]. COORDINATION CHEMISTRY REVIEWS, 1973, 10 (3-4) : 335 - 422
[3] ASLANOV LA, 1977, ZH STRUKT KHIM, V18, P1103
[4] THE STRUCTURE OF LITHIUM COMPOUNDS OF SULFONES, SULFOXIMIDES, SULFOXIDES, THIOETHERS AND 1,3-DITHIANES, NITRILES, NITRO-COMPOUNDS AND HYDRAZONES
BOCHE, G
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (03): : 277 - 297
[5] Ureas: New efficient Lewis base catalysts for the allylation of aldehydes
Chataigner, I
Piarulli, U
Gennari, C
[J]. TETRAHEDRON LETTERS, 1999, 40 (18) : 3633 - 3634
[6] REACTIVITY OF PENTACOORDINATE AND HEXACOORDINATE SILICON-COMPOUNDS AND THEIR ROLE AS REACTION INTERMEDIATES
CHUIT, C
CORRIU, RJP
REYE, C
YOUNG, JC
[J]. CHEMICAL REVIEWS, 1993, 93 (04) : 1371 - 1448
[7] Trans-effects in octahedral transition metal complexes
Coe, BJ
Glenwright, SJ
[J]. COORDINATION CHEMISTRY REVIEWS, 2000, 203 : 5 - 80
[8] Enantioselective ring opening of epoxides with silicon tetrachloride in the presence of a chiral Lewis base
Denmark, SE
Barsanti, PA
Wong, KT
Stavenger, RA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) : 2428 - 2429
[9] Solid state and solution structural studies of chiral phosphoramide-tin complexes relevant to Lewis base catalyzed aldol reactions
Denmark, SE
Su, XP
[J]. TETRAHEDRON, 1999, 55 (29) : 8727 - 8738
[10] Lewis base activation of Lewis acids. Addition of silyl ketene acetals to aldehydes
Denmark, SE
Wynn, T
Beutner, GL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (45) : 13405 - 13407

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