Highly Asymmetric Cyclopropanation With Two Sulfinyl Auxiliaries as a Way to a Useful Synthetic Intermediate

被引：1

作者：

Midura, Wanda H. ^{[1
]}

Krysiak, Jerzy ^{[1
]}

机构：

[1] Polish Acad Sci, Ctr Mol & Macromol Studies, Dept Heteroorgan Chem, PL-90363 Lodz, Poland

来源：

CHIRALITY | 2015年 / 27卷 / 11期

关键词：

asymmetric cyclopropanation; sulfoxide; phosphonate rearrangement; sulfonium ylide; sulfinyl - metal exchange; STEREOSELECTIVE-SYNTHESIS; SULFOXIDES; ANALOG; ACID; CHEMISTRY; ADDITIONS;

D O I：

10.1002/chir.22506

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The asymmetric cyclopropanation using double sulfinyl auxiliary gave bis-sulfoxide with full diastereoselectivity and very high enantioselectivity. One of the sulfinyl substituents can be removed by sulfinyl metal exchange. Differentiation of sulfinyl substituents made it possible to assign the place of attack of the Grignard reagent. Chirality 27:816-819, 2015. (c) 2015 Wiley Periodicals, Inc.

引用

页码：816 / 819

页数：4

共 30 条

[1] Convergent preparation of enantiomerically pure polyalkylated cyclopropane derivatives [J].

Abramovitch, Adi ;

Fensterbank, Lottis ;

Malacria, Max ;

Marek, Ilan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (36) :6865-6868

[2] Preparation of both enantiomers of cyclopropane derivatives from the reaction of vinyl selenones with di-(-)-bornyl malonate [J].

Bagnoli, Luana ;

Scarponi, Catalina ;

Testaferri, Lorenzo ;

Tiecco, Marcello .

TETRAHEDRON-ASYMMETRY, 2009, 20 (13) :1506-1514

[3] Asymmetric Cyclopropanation Reactions [J].

Bartoli, Giuseppe ;

Bencivenni, Giorgio ;

Dalpozzo, Renato .

SYNTHESIS-STUTTGART, 2014, 46 (08) :979-1029

[4] Highly diastereoselective Michael additions onto dienyl bis-sulfoxides [J].

Brebion, F ;

Goddard, JP ;

Fensterbank, L ;

Malacria, M .

SYNTHESIS-STUTTGART, 2005, (14) :2449-2452

[5] Diastereoselective synthesis of enantiopure acyclic β,β′-disubstituted vinylsulfoxides [J].

Brebion, Franck ;

Goddard, Jean-Philippe ;

Fensterbank, Louis ;

Malacria, Max .

ORGANIC LETTERS, 2008, 10 (10) :1917-1920

[6] Addition of bis-sulfinyl anions to ketones:: Stereoselective synthesis of allylic alcohols through Evans-Mislow rearrangement based domino reactions [J].

Brebion, Franck ;

Najera, Francisco ;

Delovrie, Benedicte ;

Lacote, Emmanuel ;

Fensterbank, Louis ;

Malacria, Max .

SYNTHESIS-STUTTGART, 2007, (15) :2273-2278

[7] Enantiopure sulfoxides: recent applications in asymmetric synthesis [J].

Carmen Carreno, M. ;

Hernandez-Torres, Gloria ;

Ribagorda, Maria ;

Urbano, Antonio .

CHEMICAL COMMUNICATIONS, 2009, (41) :6129-6144

[8]

Delouvrié B, 2002, EUR J ORG CHEM, V2002, P3507

[9] Recent developments in the synthesis and utilization of chiral sulfoxides [J].

Fernández, I ;

Khiar, N .

CHEMICAL REVIEWS, 2003, 103 (09) :3651-3705

[10] Recent developments in chiral non-racemic sulfinyl-group chemistry in asymmetric synthesis [J].

Hanquet, G ;

Colobert, F ;

Lanners, S ;

Solladié, G .

ARKIVOC, 2003, :328-401

← 1 2 3 →