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

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

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.

Original language	English
Pages (from-to)	6526-6529
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	24
DOIs	https://doi.org/10.1021/acs.orglett.7b03232
State	Published - 15 Dec 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",

volume = "19",

pages = "6526--6529",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

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

Abstract

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