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- Title
Asymmetric Traceless Petasis Borono-Mannich Reactions of Enals: Reductive Transposition of Allylic Diazenes.
- Authors
Jiang, Yao; Thomson, Regan J.; Schaus, Scott E.
- Abstract
The traceless Petasis borono-Mannich reaction of enals, sulfonylhydrazines, and allylboronates, catalyzed by chiral biphenols, results in an asymmetric reductive transposition of the in situ generated allylic diazene. Acyclic 1,4-diene products bearing either alkyl- or aryl-substituted benzylic stereocenters are afforded in excellent yields and enantiomeric ratios of up to 99:1. The use of crotylboronates in the reaction results in concomitant formation of two stereocenters in either a 1,4- syn or anti relationship from the corresponding E- or Z-crotylboronate used in the reaction. The use of β-monosubstituted enals in the asymmetric traceless Petasis borono-Mannich reaction of crotylboronates installs tertiary methyl-bearing stereocenters in good yields and high enantioselectivities.
- Subjects
DIAZENES; MANNICH reaction; ALLYLBORATION; HYDRAZINES; ARYL group
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 52, p16858
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201708784