Optimization of enantiocontrol in cis-selective cyclopropanation reactions catalyzed by dirhodium(II) tetrakis[alkyl 2-oxaazetidine-4(S)-carboxylates]

被引：45

作者：

Doyle, MP ^{[1
]}

Davies, SB ^{[1
]}

Hu, WH ^{[1
]}

机构：

[1] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA

来源：

CHEMICAL COMMUNICATIONS | 2000年 / 10期

关键词：

D O I：

10.1039/b001464h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Both intermolecular and macrocyclic intramolecular cyclopropanation reactions occur with greater selectivity for the cis-(Z)-diastereoisomer than for the trans-(E)-diastereomer in reactions catalyzed by chiral dirhodium(ii) azetidinone-carboxylates; the influence of the catalyst's ester alkyl group on enantiocontrol is substantial but appears to be delicately balanced by steric factors.

引用

页码：867 / 868

页数：2

共 14 条

[1] Asymmetric rhodium carbenoid insertion into the Si-H bond
Buck, RT
Doyle, MP
Drysdale, MJ
Ferris, L
Forbes, DC
Haigh, D
Moody, CJ
Pearson, ND
Zhou, QL
[J]. TETRAHEDRON LETTERS, 1996, 37 (42) : 7631 - 7634
[2] Recent advances in asymmetric catalytic metal carbene transformations
Doyle, MP
Forbes, DC
[J]. CHEMICAL REVIEWS, 1998, 98 (02) : 911 - 935
[3] ASYMMETRIC-SYNTHESIS OF LACTONES WITH HIGH ENANTIOSELECTIVITY BY INTRAMOLECULAR CARBON HYDROGEN INSERTION REACTIONS OF ALKYL DIAZOACETATES CATALYZED BY CHIRAL RHODIUM(II) CARBOXAMIDES
DOYLE, MP
VANOEVEREN, A
WESTRUM, LJ
PROTOPOPOVA, MN
CLAYTON, TW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) : 8982 - 8984
[4] DOYLE MP, 1993, ACS SYM SER, V517, P40
[5] Doyle MP, 1997, CHEM COMMUN, P983
[6] Comparative evaluation of enantiocontrol for intramolecular cyclopropanation of diazoacetates with chiral Cu-I, Rh-II and Ru-II catalysts
Doyle, MP
Peterson, CS
Zhou, QL
Nishiyama, H
[J]. CHEMICAL COMMUNICATIONS, 1997, (02) : 211 - 212
[7] Formation of macrocyclic lactones by enantioselective intramolecular cyclopropanation of diazoacetates catalyzed by chiral Cu-I and Rh-II compounds
Doyle, MP
Peterson, CS
Parker, DL
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (12): : 1334 - 1336
[8] Macrocycle formation by catalytic intramolecular cyclopropanation. A new general methodology for the synthesis of macrolides
Doyle, MP
Peterson, CS
Protopopova, MN
Marnett, AB
Parker, DL
Ene, DG
Lynch, V
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (38) : 8826 - 8837
[9] Doyle MP, 1996, SYNLETT, P697
[10] New aspects of catalytic asymmetric cyclopropanation
Doyle, MP
Protopopova, MN
[J]. TETRAHEDRON, 1998, 54 (28) : 7919 - 7946

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