SCHEDULED MAINTENANCE
Catalyst-controlled diastereoselectivity reversal in the formation of dihydropyrans†
Taichi
Kano, 
*a
Keiji
Maruoka
*ab
*a
Keiji
Maruoka
*ab
Abstract
An enantioselective synthesis of cis-dihydropyrans as the formal HDA reaction products was achieved through the catalyst-controlled anti-selective conjugate addition of aldehydes to β,γ-unsaturated α-keto esters. The observed unusual cis-selectivity could be attributed to the stabilization of the less favorable transition state for anti-conjugate adducts by the hydrogen bonding between the hydroxy group of the amino diol catalyst and β,γ-unsaturated α-keto esters.
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