Stereoselective arylation of substituted cyclopentenes by substrate-directable Heck–Matsuda reactions: a concise total synthesis of the sphingosine 1-phosphate …

CC Oliveira, EAF dos Santos, JHB Nunes…

Index: Oliveira, Caio C.; Dos Santos, Emerson A. F.; Bormio Nunes, Julia H.; Correia, Carlos Roque D. Journal of Organic Chemistry, 2012 , vol. 77, # 18 p. 8182 - 8190,9

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Citation Number: 23

Abstract

We describe herein an efficient and diastereoselective substrate-directable Heck–Matsuda reaction with nonactivated five-membered olefins. The carbamate acts as the main directing group in the arylation process allowing the synthesis of several functionalized aryl cyclopentenes in good to excellent diastereoselectivities (> 85: 15) and in isolated yields ranging from 41 to 90%. No double bond isomerizations were observed in these Heck ...

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