Advanced Synthesis and Catalysis 2018-04-16

Synthesis of Piperidine Derivatives by Rhodium‐ Catalyzed Tandem Reaction of N‐Sulfonyl‐1,2,3‐Triazole and Vinyl Ether

Sisi Yu; Yuehui An; Wenlin Wang; Ze‐Feng Xu; Chuan‐Ying Li

Index: 10.1002/adsc.201800191

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Abstract

A chemoselective tandem reaction of 4‐acyloxymethylene‐1‐sulfonyl‐1,2,3‐triazole and vinyl ether was reported, producing polysubstituted piperidine derivatives in up to 96% yield. The key intermediate N‐sulfonyl 1‐azadiene generated by migration of the OAc group to the α‐imino rhodium carbene was isolated and a plausible mechanism was proposed. Several related ring systems were constructed from the highly functionalized products.