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Asymmetric Petasis Borono‐Mannich Allylation Reactions Catalyzed by Chiral Biphenols
Author(s) -
Jiang Yao,
Schaus Scott E.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201611332
Subject(s) - catalysis , chemistry , mannich reaction , aldehyde , diastereomer , amine gas treating , condensation , organic chemistry , condensation reaction , combinatorial chemistry , physics , thermodynamics
Chiral biphenols catalyze the asymmetric Petasis borono‐Mannich allylation of aldehydes and amines through the use of a bench‐stable allyldioxaborolane. The reaction proceeds via a two‐step, one‐pot process and requires 2–8 mole % of 3,3′‐Ph 2 ‐BINOL as the optimal catalyst. Under microwave heating the reaction affords chiral homoallylic amines in excellent yields (up to 99 %) and high enantioselectivies (er up to 99:1). The catalytic reaction is a true multicomponent condensation reaction whereas both the aldehyde and the amine can possess a wide range of structural and electronic properties. Use of crotyldioxaborolane in the reaction results in stereodivergent products with anti‐ and syn‐diastereomers both in good diastereoselectivities and enantioselectivities from the corresponding E‐ and Z‐borolane stereoisomers.