Organic letters

Enantioselective Synthesis of 2, 6-cis-Disubstituted Tetrahydropyrans via a Tandem Catalytic Asymmetric Hydrogenation/Oxa-Michael Cyclization: An Efficient …

JH Xie, LC Guo, XH Yang, LX Wang, QL Zhou

Index: Xie, Jian-Hua; Guo, Lu-Chuan; Yang, Xiao-Hui; Wang, Li-Xin; Zhou, Qi-Lin Organic Letters, 2012 , vol. 14, # 18 p. 4758 - 4761,4

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Citation Number: 23

Abstract

A highly efficient one-pot process via a tandem reaction of catalytic asymmetric hydrogenation and oxa-Michael cyclization for the synthesis of 2, 6-cis-disubstituted tetrahydropyrans has been developed (ee up to 99.9%, cis/trans-selectivity up to 99: 1). This method provides a concise route to (−)-centrolobine (68.8% yield, three steps).