Diastereoselective Coupling of Chiral Acetonide Trisubstituted Radicals with Alkenes

Daniel J Tao; Mikko Muuronen; Yuriy Slutskyy; Alexander Le; Filipp Furche; Larry E Overman

doi:10.1002/chem.201601957

Diastereoselective Coupling of Chiral Acetonide Trisubstituted Radicals with Alkenes

Chemistry. 2016 Jun 20;22(26):8786-90. doi: 10.1002/chem.201601957. Epub 2016 May 30.

Authors

Daniel J Tao¹, Mikko Muuronen¹, Yuriy Slutskyy¹, Alexander Le¹, Filipp Furche², Larry E Overman³

Affiliations

¹ Department of Chemistry, University of California Irvine, 1102 Natural Sciences II, Irvine, CA, 92697-2025, USA.
² Department of Chemistry, University of California Irvine, 1102 Natural Sciences II, Irvine, CA, 92697-2025, USA. filipp.furche@uci.edu.
³ Department of Chemistry, University of California Irvine, 1102 Natural Sciences II, Irvine, CA, 92697-2025, USA. leoverma@uci.edu.

Abstract

The stereochemical outcome of reactions of chiral nucleophilic trisubstituted acetonide radicals with electron-deficient alkenes is dictated by a delicate balance between destabilizing non-bonding interactions and stabilizing hydrogen-bonding between substituents on the α and β carbons.

Keywords: ab initio calculations; alkenes; radical reactions; stereoselectivity.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Alkenes / chemistry*
Carbon / chemistry
Catalysis
Free Radicals / chemistry
Light
Molecular Conformation
Stereoisomerism

Substances

Alkenes
Free Radicals
Carbon

Abstract

Publication types

MeSH terms

Substances

Grants and funding