Diastereoselective titanium-mediated construction of cis-2,3-ring annelated 1-(2′-chloroethyl)cyclopropanols

被引:20
作者
Lecornué, F [1 ]
Ollivier, J [1 ]
机构
[1] Univ Paris 11, Inst Chim Mol & Mat Orsay, UMR 8615, Lab Carbocycles, F-91405 Orsay, France
关键词
D O I
10.1039/b211642a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Titanium(IV)-mediated cyclopropanation induced by reaction of cycloalkylmagnesium bromides 1a-e in the presence of titanium tetraisopropoxide with ethyl beta-chloropropionate 2 yielded cis-fused 1-(2'-chloroethyl) cyclopropanols 3b-e with diastereoselectivity highly depending on the ring size. Unexpected rearrangement products 5d, e were isolated in some cases.
引用
收藏
页码:584 / 585
页数:2
相关论文
共 22 条
[1]  
Chaplinski V, 1997, SYNLETT, P111
[2]   Titanium-mediated formation of 1,2-disubstituted cyclopropanols from esters and alkenes. A new approach to the synthesis of 3,11-dimethylnonacosan-2-one, a sex pheromone of the German cockroach [J].
Epstein, OL ;
Kulinkovich, OG .
TETRAHEDRON LETTERS, 1998, 39 (13) :1823-1826
[3]   A FACILE CYCLOPROPANOL SYNTHESIS FROM BETA-HALO ESTER WITH GRIGNARD REAGENT-SAMARIUM(II) DIIODIDE COUPLE [J].
FUKUZAWA, S ;
NIIMOTO, Y ;
SAKAI, S .
TETRAHEDRON LETTERS, 1991, 32 (52) :7691-7694
[4]   Magnesium bromide promoted barbier-type intramolecular cyclization of halo-substituted acetals, ketals, and orthoesters [J].
Huang, JW ;
Chen, CD ;
Leung, MK .
TETRAHEDRON LETTERS, 1999, 40 (49) :8647-8650
[5]   REACTIONS OF CARBONYL-COMPOUNDS WITH BENZYL CHLOROMETHYL ETHER OF DIIODOMETHANE IN THE PRESENCE OF SAMARIUM(II) IODIDE OR METALLIC SAMARIUM - NEW ROUTES TO 1,2-DIOLS, IODOHYDRINS AND CYCLOPROPANOLS [J].
IMAMOTO, T ;
HATAJIMA, T ;
TAKIYAMA, N ;
TAKEYAMA, T ;
KAMIYA, Y ;
YOSHIZAWA, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (12) :3127-3135
[6]   1,n-dicarbanionic titanium intermediates from monocarbanionic organometallics and their application in organic synthesis [J].
Kulinkovich, OG ;
de Meijere, A .
CHEMICAL REVIEWS, 2000, 100 (08) :2789-2834
[7]  
KULINKOVICH OG, 1991, ZH ORG KHIM+, V27, P294
[8]  
KULINKOVICH OG, 1989, ZH ORG KHIM+, V25, P2244
[9]   TITANIUM(IV) ISOPROPOXIDE-CATALYZED FORMATION OF 1-SUBSTITUTED CYCLOPROPANOLS IN THE REACTION OF ETHYLMAGNESIUM BROMIDE WITH METHYL ALKANECARBOXYLATES [J].
KULINKOVICH, OG ;
SVIRIDOV, SV ;
VASILEVSKI, DA .
SYNTHESIS-STUTTGART, 1991, (03) :234-234
[10]   A new variant of the Kulinkovich hydroxycyclopropanation. Reductive coupling of carboxylic esters with terminal olefins [J].
Lee, J ;
Kim, H ;
Cha, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (17) :4198-4199