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Full Paper
Construction of Functionalized Carbocycles Having Contiguous Tertiary Carbinol and All-Carbon Stereogenic Centers
Article first published online: 1 MAR 2013
DOI: 10.1002/ejoc.201201382
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Reddy, C., Babu, S. A., Aslam, N. A. and Rajkumar, V. (2013), Construction of Functionalized Carbocycles Having Contiguous Tertiary Carbinol and All-Carbon Stereogenic Centers. Eur. J. Org. Chem., 2013: 2362–2380. doi: 10.1002/ejoc.201201382
Publication History
- Issue published online: 10 APR 2013
- Article first published online: 1 MAR 2013
- Manuscript Received: 18 OCT 2012
Keywords:
- Carbocycles;
- Allylation;
- Diastereoselectivity;
- Indium;
- Lactones;
- Configuration determination
Abstract
A highly stereoselective protocol is reported for customizing functionalized carbocyclic building blocks (β-hydroxy esters) and bicyclic lactones with a stereoarray that contains contiguous tertiary carbinol and all-carbon stereocenters. The efficient asymmetric induction and diastereofacial selective addition of allyl and propargyl indiums to hindered α,α-disubstituted cycloalkanones is presented. The stereochemistry of representative products was unequivocally established from single-crystal X-ray crystal structure analyses, and a plausible reaction pathway was proposed to support the high diastereofacial selectivity.