Highly Efficient Organocatalytic Kinetic Resolution of Activated Nitroallylic Acetates with Aldehydes via Conjugate Addition−Elimination

A novel, efficient, and unprecedented organocatalytic kinetic resolution has been developed. For the first time, a variety of nitroallylic acetates 1a−i have been resolved with aldehydes in the presence of 2 (2.5 mol %) via conjugate addition−elimination. The densely functionalized products 3a−o wer...

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Bibliographic Details
Published inOrganic letters Vol. 13; no. 6; pp. 1458 - 1461
Main Authors Reddy, Raju Jannapu, Chen, Kwunmin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.03.2011
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALCOHOLS
INDOLINES
ION
ETHERS
ALLYLIC ALKYLATIONS
MICHAEL ADDITION
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Summary:A novel, efficient, and unprecedented organocatalytic kinetic resolution has been developed. For the first time, a variety of nitroallylic acetates 1a−i have been resolved with aldehydes in the presence of 2 (2.5 mol %) via conjugate addition−elimination. The densely functionalized products 3a−o were obtained with excellent enantioselectivities (up to >99% ee), and unreacted substrates 1a−i were recovered with good to excellent optical purity (up to 98% ee).
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol200133y