Computational study of the stereochemistry of intramolecular carbolithiation of an alkene by a secondary alkyllithium: stereochemistry change caused by a single THF molecule of solvation.

Liu, Hanbin and Deng, Kai and Cohen, Theodore and Jordan, Kenneth D (2007) Computational study of the stereochemistry of intramolecular carbolithiation of an alkene by a secondary alkyllithium: stereochemistry change caused by a single THF molecule of solvation. Org Lett, 9 (10). 1911 - 1914. ISSN 1523-7060

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Abstract

Theoretical calculations reveal that the 40:1 ratio of trans- to cis-2-methylcyclopentylmethyllithium formed in the cyclization of 6-lithio-1-heptene by intramolecular carbolithiation is due to steric crowding in the transition state for the cis-cyclization pathway when a single THF molecule complexes the lithium cation. In the absence of this specific solvation, the cis-cyclization pathway is predicted to be slightly favored.

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Details

Item Type:	Article
Status:	Published
Creators/Authors:	Creators Email Pitt Username ORCID Liu, Hanbin Deng, Kai Cohen, Theodore Jordan, Kenneth D jordan@pitt.edu JORDAN
Date:	10 May 2007
Date Type:	Publication
Journal or Publication Title:	Org Lett
Volume:	9
Number:	10
Page Range:	1911 - 1914
DOI or Unique Handle:	10.1021/ol070453+
Schools and Programs:	Dietrich School of Arts and Sciences > Chemistry
Refereed:	Yes
ISSN:	1523-7060
PubMed ID:	17439226
Date Deposited:	29 Oct 2012 21:21
Last Modified:	21 May 2021 10:56
URI:	http://d-scholarship.pitt.edu/id/eprint/16080

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