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

Mehta, Goverdhan ; Ravikrishna, Chebolu ; Kalyanaraman, Pattabiraman ; Chandrasekhar, Jayaraman (1998) Nucleophilic additions to 4-substituted snoutanones: getting a measure of long range electrostatic and orbital control of π-face selectivity Journal of the Chemical Society, Perkin Transactions 1 (12). pp. 1895-1898. ISSN 0300-922X

Preview

PDF - Publisher Version
155kB

Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/1998...

Related URL: http://dx.doi.org/10.1039/A802254B

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 π-face selectivity in the latter systems.

Item Type:	Article
Source:	Copyright of this article belongs to Royal Society of Chemistry.
ID Code:	29046
Deposited On:	18 Dec 2010 05:40
Last Modified:	17 May 2016 12:01

Repository Staff Only: item control page