Asymmetric ring opening of meso epoxides with TMSCN catalyzed by (pybox)lanthanide complexes

被引：171

作者：

Schaus, SE ^{[1
]}

Jacobsen, EN ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 07期

关键词：

D O I：

10.1021/ol005721h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The asymmetric ring opening of meso epoxides with TMSCN is catalyzed by (pybox)YbCl3 complexes, yielding the beta-trimethylsilyloxy nitrile ring-opened products with good enantioselectivities (83-92% ee). The reaction exhibits a second-order kinetic dependence on catalyst concentration and a first-order dependence on epoxide concentration, consistent with a bimetallic pathway involving simulataneous activation of epoxide and cyanide.

引用

页码：1001 / 1004

页数：4

共 41 条

[1] Catalytic, asymmetric cyanohydrin synthesis mediated by lanthanide(III) chloride pybox complexes
Aspinall, HC
Greeves, N
Smith, PM
[J]. TETRAHEDRON LETTERS, 1999, 40 (09) : 1763 - 1766
[2] EASY DIRECT STEREOSELECTIVE AND REGIOSELECTIVE FORMATION OF BETA-HYDROXY NITRILES BY REACTION OF 1,2-EPOXIDES WITH POTASSIUM CYANIDE IN THE PRESENCE OF METAL-SALTS
CHINI, M
CROTTI, P
FAVERO, L
MACCHIA, F
[J]. TETRAHEDRON LETTERS, 1991, 32 (36) : 4775 - 4778
[3] CHOUDRY BM, 1971, SYNTHETIC COMMUN, V25, P2829
[4] Discovery of chiral catalysts through ligand diversity: Ti-catalyzed enantioselective addition of TMSCN to meso epoxides
Cole, BM
Shimizu, KD
Krueger, CA
Harrity, JPA
Snapper, ML
Hoveyda, AH
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (15): : 1668 - 1671
[5] Crotti P, 1997, GAZZ CHIM ITAL, V127, P273
[6] 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
[7] C2-symmetric copper(II) complexes as chiral Lewis acids.: Scope and mechanism of catalytic enantioselective aldol additions of enolsilanes to (benzyloxy)acetaldehyde
Evans, DA
Kozlowski, MC
Murry, JA
Burgey, CS
Campos, KR
Connell, BT
Staples, RJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (04) : 669 - 685
[8] Reversal in enantioselectivity of tert-butyl versus phenyl-substituted bis(oxazoline)copper(II) catalyzed hetero Diels-Alder and ene reactions.: Crystallographic and mechanistic studies
Evans, DA
Johnson, JS
Burgey, CS
Campos, KR
[J]. TETRAHEDRON LETTERS, 1999, 40 (15) : 2879 - 2882
[9] GASSMAN PG, 1985, ORG SYNTH, V64, P39
[10] GASSMAN PG, 1982, J AM CHEM SOC, V104, P1849

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