Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 52, Pages 16631-16635Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201708784
Keywords
allylic compounds; asymmetric synthesis; hydrazones; organocatalysis; rearrangements
Categories
Funding
- National Institutes of Health [R01 GM078240]
- National Science Foundation [CHE1361173]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1361173] Funding Source: National Science Foundation
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The traceless Petasis borono-Mannich reaction of enals, sulfonylhydrazines, and allylboronates, catalyzed by chiral biphenols, results in an asymmetric reductive transposition of the insitu 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 beta-monosubstituted enals in the asymmetric traceless Petasis borono-Mannich reaction of crotylboronates installs tertiary methyl-bearing stereocenters in good yields and high enantioselectivities.
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