Divergent Access to Functionalized Pyrrolidines and Pyrrolines via Iridium-Catalyzed Domino-Ring-Opening Cyclization of Vinyl Aziridines with β-Ketocarbonyls

Tao Yan Lin; Hai Hong Wu; Jian Jun Feng; Junliang Zhang

doi:10.1021/acs.orglett.7b03232

Divergent Access to Functionalized Pyrrolidines and Pyrrolines via Iridium-Catalyzed Domino-Ring-Opening Cyclization of Vinyl Aziridines with β-Ketocarbonyls

Tao Yan Lin
, Hai Hong Wu
, Jian Jun Feng^*
, Junliang Zhang

^*此作品的通讯作者

化学与分子工程学院

East China Normal University

科研成果: 期刊稿件 › 文章 › 同行评审

31 引用（Scopus）

摘要

A useful synthesis of five-membered N-heterocycles has been developed through an iridium-catalyzed domino-ring-opening cyclization of vinylaziridines with β-ketocarbonyls. α-Substituted 1,3-dicarbonyls reacted with vinylaziridines to give 2-methylenepyrrolidines bearing two adjacent sp³-carbon centers with moderate to excellent diastereoselectivity, while the reaction of α-unsubstituted 1,3-dicarbonyls afforded 2-pyrrolines in good yield.

源语言	英语
页（从-至）	6526-6529
页数	4
期刊	Organic Letters
卷	19
期	24
DOI	https://doi.org/10.1021/acs.orglett.7b03232
出版状态	已出版 - 15 12月 2017

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title = "Divergent Access to Functionalized Pyrrolidines and Pyrrolines via Iridium-Catalyzed Domino-Ring-Opening Cyclization of Vinyl Aziridines with β-Ketocarbonyls",

abstract = "A useful synthesis of five-membered N-heterocycles has been developed through an iridium-catalyzed domino-ring-opening cyclization of vinylaziridines with β-ketocarbonyls. α-Substituted 1,3-dicarbonyls reacted with vinylaziridines to give 2-methylenepyrrolidines bearing two adjacent sp3-carbon centers with moderate to excellent diastereoselectivity, while the reaction of α-unsubstituted 1,3-dicarbonyls afforded 2-pyrrolines in good yield.",

author = "Lin, \{Tao Yan\} and Wu, \{Hai Hong\} and Feng, \{Jian Jun\} and Junliang Zhang",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

month = dec,

day = "15",

doi = "10.1021/acs.orglett.7b03232",

language = "英语",

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T1 - Divergent Access to Functionalized Pyrrolidines and Pyrrolines via Iridium-Catalyzed Domino-Ring-Opening Cyclization of Vinyl Aziridines with β-Ketocarbonyls

AU - Lin, Tao Yan

AU - Wu, Hai Hong

AU - Feng, Jian Jun

AU - Zhang, Junliang

PY - 2017/12/15

Y1 - 2017/12/15

N2 - A useful synthesis of five-membered N-heterocycles has been developed through an iridium-catalyzed domino-ring-opening cyclization of vinylaziridines with β-ketocarbonyls. α-Substituted 1,3-dicarbonyls reacted with vinylaziridines to give 2-methylenepyrrolidines bearing two adjacent sp3-carbon centers with moderate to excellent diastereoselectivity, while the reaction of α-unsubstituted 1,3-dicarbonyls afforded 2-pyrrolines in good yield.

AB - A useful synthesis of five-membered N-heterocycles has been developed through an iridium-catalyzed domino-ring-opening cyclization of vinylaziridines with β-ketocarbonyls. α-Substituted 1,3-dicarbonyls reacted with vinylaziridines to give 2-methylenepyrrolidines bearing two adjacent sp3-carbon centers with moderate to excellent diastereoselectivity, while the reaction of α-unsubstituted 1,3-dicarbonyls afforded 2-pyrrolines in good yield.

UR - https://www.scopus.com/pages/publications/85038434379

U2 - 10.1021/acs.orglett.7b03232

DO - 10.1021/acs.orglett.7b03232

M3 - 文章

C2 - 29164890

AN - SCOPUS:85038434379

SN - 1523-7060

VL - 19

SP - 6526

EP - 6529

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

Divergent Access to Functionalized Pyrrolidines and Pyrrolines via Iridium-Catalyzed Domino-Ring-Opening Cyclization of Vinyl Aziridines with β-Ketocarbonyls

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