Creating quaternary centers with high exo stereoselectivity using activated alpha-alkynyl dienophiles

Authors
Min, Sun-JoonJones, Gavin O.Houk, K. N.Danishefsky, Samuel J.
Issue Date
2007-08-22
Publisher
AMER CHEMICAL SOC
Citation
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.129, no.33, pp.10078 - +
Abstract
Ethynyl substituents were used to direct a highly exoselective creation of quaternary carbon centers in Diels-Alder cycloaddition reactions involving activated alpha-alkynyl dienophiles. The origins of electronic activation and the high stereoselectivities of these reactions were investigated by the B3LYP density functional method.
Keywords
DIELS-ALDER REACTIONS; SECONDARY ORBITAL INTERACTIONS; VIBRATIONAL ABSORPTION; STEREOGENIC CENTERS; PAECILOMYCINE-A; ACIDITY TRENDS; DENSITY; STEREOCENTERS; DIELS-ALDER REACTIONS; SECONDARY ORBITAL INTERACTIONS; VIBRATIONAL ABSORPTION; STEREOGENIC CENTERS; PAECILOMYCINE-A; ACIDITY TRENDS; DENSITY; STEREOCENTERS
ISSN
0002-7863
URI
https://pubs.kist.re.kr/handle/201004/134189
DOI
10.1021/ja073528d
Appears in Collections:
KIST Article > 2007
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