ALPHA-HYDROXY ESTERS AS INEXPENSIVE CHIRAL AUXILIARIES IN RHODIUM(II)-CATALYZED CYCLOPROPANATIONS WITH VINYLDIAZOMETHANES

被引：47

作者：

DAVIES, HML

CANTRELL, WR

机构：

[1] Department of Chemistry, Wake Forest University, Winston-Salem, NC 27109

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 45期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/0040-4039(91)80206-L

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

High levels of asymmetric induction were achieved in rhodium(II) catalyzed cyclopropanations with chiral vinyldiazomethanes. (R)-(-)-Pantolactone is the most effective chiral auxiliary, but other alpha-hydroxy esters also give reasonable levels of diastereoselectivity.

引用

页码：6509 / 6512

页数：4

共 25 条

[1] ASYMMETRIC-SYNTHESIS OF PERMETHRIC ACID - STEREOCHEMISTRY OF CHIRAL COPPER CARBENOID REACTION
ARATANI, T
YONEYOSHI, Y
NAGASE, T
[J]. TETRAHEDRON LETTERS, 1982, 23 (06) : 685 - 688
[2] CANTRELL WR, 1991, J ORG CHEM, V56, P7230
[3] A GREATLY IMPROVED PROCEDURE FOR RUTHENIUM TETRAOXIDE CATALYZED OXIDATIONS OF ORGANIC-COMPOUNDS
CARLSEN, PHJ
KATSUKI, T
MARTIN, VS
SHARPLESS, KB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (19) : 3936 - 3938
[4] STEREOSELECTIVE SYNTHESIS OF 7-MEMBERED CARBOCYCLES BY A TANDEM CYCLOPROPANATION COPE REARRANGEMENT BETWEEN RHODIUM(II)-STABILIZED VINYLCARBENOIDS AND DIENES
DAVIES, HML
CLARK, TJ
SMITH, HD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) : 3817 - 3824
[5] SCOPE AND STEREOCHEMISTRY OF THE TANDEM INTRAMOLECULAR CYCLOPROPANATION COPE REARRANGEMENT SEQUENCE
DAVIES, HML
MCAFEE, MJ
OLDENBURG, CEM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (04) : 930 - 936
[6] STEREOSELECTIVE CYCLOPROPANATIONS WITH VINYLCARBENOIDS
DAVIES, HML
CLARK, TJ
CHURCH, LA
[J]. TETRAHEDRON LETTERS, 1989, 30 (38) : 5057 - 5060
[7] CATALYTIC METHODS FOR METAL CARBENE TRANSFORMATIONS
DOYLE, MP
[J]. CHEMICAL REVIEWS, 1986, 86 (05) : 919 - 939
[8] SYNTHESIS AND CATALYTIC REACTIONS OF CHIRAL N-(DIAZOACETYL)OXAZOLIDONES
DOYLE, MP
DOROW, RL
TERPSTRA, JW
RODENHOUSE, RA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (10) : 1663 - 1666
[9] HIGH ENANTIOSELECTIVITY IN THE INTRAMOLECULAR CYCLOPROPANATION OF ALLYL DIAZOACETATES USING A NOVEL RHODIUM(II) CATALYST
DOYLE, MP
PIETERS, RJ
MARTIN, SF
AUSTIN, RE
OALMANN, CJ
MULLER, P
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (04) : 1423 - 1424
[10] CHIRAL RHODIUM(II) CARBOXAMIDES - A NEW CLASS OF CATALYSTS FOR ENANTIOSELECTIVE CYCLOPROPANATION REACTIONS
DOYLE, MP
BRANDES, BD
KAZALA, AP
PIETERS, RJ
JARSTFER, MB
WATKINS, LM
EAGLE, CT
[J]. TETRAHEDRON LETTERS, 1990, 31 (46) : 6613 - 6616

← 1 2 3 →