Asymmetric Petasis reactions catalyzed by chiral biphenols
Asymmetric Petasis reactions catalyzed by chiral biphenols
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DOI：
10.1021/ja8018934
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发表时间：
2008-06-04
影响因子：
15
通讯作者：
Schaus, Scott E.
中科院分区：
文献类型：
--
作者：
Lou, Sha;Schaus, Scott E.
Chiral biphenols catalyze the enantioselective Petasis reaction of alkenyl boronates, secondary amines, and ethyl glyoxylate. The reaction requires the use of 15 mol % of (S)-VAPOL as the catalyst, alkenyl boronates as nucleophiles, ethyl glyoxylate as the aldehyde component, and 3 A molecular sieves as an additive. The chiral alpha-amino ester products are obtained in good yields (71-92%) and high enantiomeric ratios (89:11-98:2). Mechanistic investigations indicate single ligand exchange of acyclic boronate with VAPOL and tetracoordinate boronate intermediates.
