SmI2-Mediated Radical Cross-Couplings of α-Hydroxylated Aza-hemiacetals and N, S-Acetals with α, β-Unsaturated Compounds: Asymmetric Synthesis of (+)- …

…, YG Xiang, YP Ruan, X Zheng, PQ Huang

Index: Liu, Xue-Kui; Qiu, Shi; Xiang, Yong-Gang; Ruan, Yuan-Ping; Zheng, Xiao; Huang, Pei-Qiang Journal of Organic Chemistry, 2011 , vol. 76, # 12 p. 4952 - 4963

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Citation Number: 34

Abstract

The SmI2-mediated radical coupling reactions of β-hydroxylated pyrrolidine/piperidine aza- hemiacetals 8 and 9 and N, S-acetals 6 and 33 with α, β-unsaturated compounds are described. This method allows a rapid access to β-hydroxylated pyrrolidines, piperidines, pyrrolizidinones, and indolizidinones. Starting from N, S-acetal 33 and via a common intermediate 27, the alkaloids hyacinthacine A2 (2), uniflorine A (3, 6-epi-casuarine), and ...