Enantiospecific Photochemical Norrish/Yang Type II Reaction of Nonbiaryl Atropchiral α-Oxoamides in Solution—Axial to Point Chirality Transfer

α-Oxoamides 1 with o-tert-butyl substitution on the N-phenyl moiety were found to be stable axially chiral atropisomers. These axially chiral α-oxoamides undergo enantiospecific photochemical γ-Hydrogen abstraction in CHCl3 to yield β-lactams with high enantioselectivity (e.r. ∼90:10) in solution. T...

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Published inJournal of the American Chemical Society Vol. 131; no. 32; pp. 11314 - 11315
Main Authors Ayitou, Anoklase Jean-Luc, Jesuraj, Josepha L., Barooah, Nilotpal, Ugrinov, Angel, Sivaguru, J.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.08.2009
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
LACTAM
LIGANDS
ASYMMETRIC INDUCTION
RING
PHOTOCYCLIZATION
AUXILIARY
AMIDES
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Summary:α-Oxoamides 1 with o-tert-butyl substitution on the N-phenyl moiety were found to be stable axially chiral atropisomers. These axially chiral α-oxoamides undergo enantiospecific photochemical γ-Hydrogen abstraction in CHCl3 to yield β-lactams with high enantioselectivity (e.r. ∼90:10) in solution. The extent of enantioselectivity was found to be dependent on the reaction temperature.
Bibliography:National Science Foundation
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja9050586