3 years ago

Asymmetric Traceless Petasis Borono-Mannich Reactions of Enals: Reductive Transpositions of Allylic Diazenes

Scott E. Schaus, Regan J Thomson, Yao Jiang
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 alkyl- or aryl- substituted benzylic stereocenters are afforded in excellent yields and enantiomeric ratios up to 99:1. The use of crotylboronates in the reaction results in concomitant formation of two stereocenters in a 1,4-syn or anti relationship from the corresponding E- or Z-crotylboronate used in the reaction. The use of beta mono-substituted enals in the asymmetric traceless Petasis borono-Mannich reaction of crotylboronates installs tertiary methyl-bearing stereocenters in good yields and high enantioselectivities.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201708784

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