Geminal acylation of α-heterosubstituted cyclohexanones and their ketals-Reference-Cited by-同舟云学术

Geminal acylation of α-heterosubstituted cyclohexanones and their ketals

Published:2010-11 Issue:11 Volume:88 Page:1118-1124
ISSN:0008-4042
Container-title:Canadian Journal of Chemistry
language:en
Short-container-title:Can. J. Chem.

Author:

Pottie Ian R.¹²³,Crane Sheldon N.¹²³,Gosse Anna Lee¹²³,Miller David O.¹²³,Burnell D. Jean¹²³

Affiliation:

1. Department of Chemistry and Physics, Mount Saint Vincent University, Halifax, NS B3M 2J6, Canada.

2. Department of Chemistry, Memorial University of Newfoundland, St. John’s, NL A1B 3X7, Canada.

3. Department of Chemistry, Dalhousie University, Halifax, NS B3H 4J3, Canada.

Abstract

Geminal acylation of derivatives of cyclohexanone with Br, Cl, F, and OCH3 in the α position, and of their corresponding dimethyl ketals, could not be accomplished to a significant extent following published procedures. The transformation was accomplished in two steps. The initial BF3·Et2O-mediated reaction with 1,2-bis(trimethylsilyloxy)cyclobutene gave a cyclobutanone product as a mixture of diastereomers. Only with 2-chlorocyclohexanone did this occur with good diastereoselectivity. Then, pinacol rearrangement of the diastereomeric mixture mediated by Amberlyst-15 in benzene provided the heterosubstituted spirocyclic diketone.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Link

http://www.nrcresearchpress.com/doi/pdf/10.1139/V10-097

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