Nucleophilic additions to 4-substituted snoutanones: getting a measure of long range electrostatic and orbital control of pi-face selectivity

Mehta, Goverdhan and Ravikrishna, Chebolu and Kalyanaraman, Pattabiraman and Chandrasekhar, Jayaraman (1998) Nucleophilic additions to 4-substituted snoutanones: getting a measure of long range electrostatic and orbital control of pi-face selectivity. In: Perkin Transactions 1 (12). pp. 1895-1897.

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Abstract

Pentacyclic ketones 10a-e (snoutan-9-ones) undergo nucleophilic additions with the same facial preference as the corresponding norsnoutanones 9a-e, but with markedly reduced selectivity, revealing the involvement of electrostatic effects in the former and implying the importance of hyperconjugative orbital interactions in determining pi-face selectivity in the latter systems.

Item Type:	Journal Article
Publication:	Perkin Transactions 1
Publisher:	Royal Society of Chemistry
Additional Information:	Copyright of this article belongs to Royal Society of Chemistry.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	15 Dec 2009 10:58
Last Modified:	19 Sep 2010 05:28
URI:	http://eprints.iisc.ac.in/id/eprint/19519

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