Title Total Syntheses of Vicinal Dichloride Monoterpenes Enabled by Aza-Bellus-Claisen Rearrangement
Authors Cheng, Jiangqun
Li, Yuan-He
Huang, Jun
Yang, Zhen
Affiliation Peking Univ, State Key Lab Chem Oncogen, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China
Peking Univ, Key Lab Chem Genom, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China
Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China
Peking Univ, Beijing Natl Lab Mol Sci BNLMS, Beijing 100871, Peoples R China
Keywords STEREOSELECTIVE-SYNTHESIS
HALOGENATED MONOTERPENES
RED
DIHALOGENATION
IDENTIFICATION
REDUCTION
ALCOHOL
Issue Date 5-Nov-2021
Publisher ORGANIC LETTERS
Abstract Diastereoselective syntheses of syn- and anti-vicinal dihalides were achieved via an aza Bellus-Claisen rearrangement, which involved the reaction of an alpha-chloro carboxylic acid chloride with halogen-substituted trans-allyl morpholines in the presence of Lewis acids. The developed method was used for the total synthesis of a group of monoterpene natural products bearing vicinal dichloride subunits.
URI http://hdl.handle.net/20.500.11897/629287
ISSN 1523-7060
DOI 10.1021/acs.orglett.1c03187
Indexed SCI(E)
Appears in Collections: 化学生物学与生物技术学院
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生物有机与分子工程教育部重点实验室

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