Issue 5, 2003

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

Abstract

Titanium(IV)-mediated cyclopropanation induced by reaction of cycloalkylmagnesium bromides 1ae in the presence of titanium tetraisopropoxide with ethyl β-chloropropionate 2 yielded cis-fused 1-(2′-chloroethyl)cyclopropanols 3be with diastereoselectivity highly depending on the ring size. Unexpected rearrangement products 5d,e were isolated in some cases.

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

Supplementary files

Article information

Article type
Communication
Submitted
27 Nov 2002
Accepted
22 Jan 2003
First published
29 Jan 2003

Chem. Commun., 2003, 584-585

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

F. Lecornué and J. Ollivier, Chem. Commun., 2003, 584 DOI: 10.1039/B211642A

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