Highly Enantio- and Diastereoselective Tandem Generation of Cyclopropyl Alcohols with Up to Four Contiguous Stereocenters

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2005 Sep 22

PMID 16173729

Citations 6

Authors

Hun Young Kim

Alice E Lurain

Patricia Garcia-Garcia

Patrick J Carroll

Patrick J Walsh

Affiliations

Soon will be listed here.

Abstract

Three highly enantio- and diastereoselective one-pot procedures for the synthesis of cyclopropyl and iodocyclopropyl alcohols with up to four contiguous stereocenters are reported. Route 1 involves asymmetric addition of an alkylzinc reagent to an enal followed by diastereoselective cyclopropanation. Route 2 parallels route 1, except that iodoform is used to generate the zinc carbenoid, and the products are iodocyclopropyl alcohols. Route 3 entails asymmetric vinylation of an aldehyde with divinylzinc reagents and subsequent diastereoselective cyclopropanation.

Citing Articles

Divergent Synthesis of Cyclopropane-Containing Lead-Like Compounds, Fragments and Building Blocks through a Cobalt Catalyzed Cyclopropanation of Phenyl Vinyl Sulfide.

Chawner S, Cases-Thomas M, Bull J European J Org Chem. 2017; 2017(34):5015-5024.

PMID: 28983191 PMC: 5601191. DOI: 10.1002/ejoc.201701030.

Stereoselective synthesis of β-hydroxy enamines, aminocyclopropanes, and 1,3-amino alcohols via asymmetric catalysis.

Valenta P, Carroll P, Walsh P J Am Chem Soc. 2010; 132(40):14179-90.

PMID: 20853837 PMC: 3014220. DOI: 10.1021/ja105435y.

One-pot catalytic enantio- and diastereoselective syntheses of anti-, syn-cis-disubstituted, and syn-vinyl cyclopropyl alcohols.

Kim H, Salvi L, Carroll P, Walsh P J Am Chem Soc. 2009; 132(1):402-12.

PMID: 19954146 PMC: 2805046. DOI: 10.1021/ja907781t.

One-pot multicomponent coupling methods for the synthesis of diastereo- and enantioenriched (Z)-trisubstituted allylic alcohols.

Kerrigan M, Jeon S, Chen Y, Salvi L, Carroll P, Walsh P J Am Chem Soc. 2009; 131(24):8434-45.

PMID: 19476375 PMC: 2749706. DOI: 10.1021/ja809821x.

Highly enantio- and diastereoselective one-pot methods for the synthesis of halocyclopropyl alcohols.

Kim H, Salvi L, Carroll P, Walsh P J Am Chem Soc. 2009; 131(3):954-62.

PMID: 19154172 PMC: 2646170. DOI: 10.1021/ja806989n.