Organocatalytic asymmetric α-amination of unprotected 3-aryl and 3-aliphatic substituted oxindoles using di-tert-butyl azodicarboxylate

Feng Zhou; Miao Ding; Yun Lin Liu; Cui Hong Wang; Cong Bin Ji; Yi Yu Zhang; Jian Zhou

doi:10.1002/adsc.201100379

Organocatalytic asymmetric α-amination of unprotected 3-aryl and 3-aliphatic substituted oxindoles using di-tert-butyl azodicarboxylate

Feng Zhou
, Miao Ding
, Yun Lin Liu
, Cui Hong Wang
, Cong Bin Ji
, Yi Yu Zhang
, Jian Zhou^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

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

78 Scopus citations

Abstract

The bifunctional quinine-derived thiourea catalyst 14 was found to catalyze the direct amination of unprotected 3-aryl and aliphatic substituted oxindoles with di-tert-butyl azodicarboxylate (DBAD) to construct a tetrasubstituted stereogenic carbon center at the C-3 position of oxindoles in good to excellent yield and enantioselectivity.

Original language	English
Pages (from-to)	2945-2952
Number of pages	8
Journal	Advanced Synthesis and Catalysis
Volume	353
Issue number	16
DOIs	https://doi.org/10.1002/adsc.201100379
State	Published - Nov 2011

Keywords

3-aminooxindoles
asymmetric catalysis
atom efficiency
organocatalysis
tetrasubstituted stereogenic carbon centers

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title = "Organocatalytic asymmetric α-amination of unprotected 3-aryl and 3-aliphatic substituted oxindoles using di-tert-butyl azodicarboxylate",

abstract = "The bifunctional quinine-derived thiourea catalyst 14 was found to catalyze the direct amination of unprotected 3-aryl and aliphatic substituted oxindoles with di-tert-butyl azodicarboxylate (DBAD) to construct a tetrasubstituted stereogenic carbon center at the C-3 position of oxindoles in good to excellent yield and enantioselectivity.",

keywords = "3-aminooxindoles, asymmetric catalysis, atom efficiency, organocatalysis, tetrasubstituted stereogenic carbon centers",

author = "Feng Zhou and Miao Ding and Liu, \{Yun Lin\} and Wang, \{Cui Hong\} and Ji, \{Cong Bin\} and Zhang, \{Yi Yu\} and Jian Zhou",

year = "2011",

month = nov,

doi = "10.1002/adsc.201100379",

language = "英语",

volume = "353",

pages = "2945--2952",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

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number = "16",

}

TY - JOUR

T1 - Organocatalytic asymmetric α-amination of unprotected 3-aryl and 3-aliphatic substituted oxindoles using di-tert-butyl azodicarboxylate

AU - Zhou, Feng

AU - Ding, Miao

AU - Liu, Yun Lin

AU - Wang, Cui Hong

AU - Ji, Cong Bin

AU - Zhang, Yi Yu

AU - Zhou, Jian

PY - 2011/11

Y1 - 2011/11

N2 - The bifunctional quinine-derived thiourea catalyst 14 was found to catalyze the direct amination of unprotected 3-aryl and aliphatic substituted oxindoles with di-tert-butyl azodicarboxylate (DBAD) to construct a tetrasubstituted stereogenic carbon center at the C-3 position of oxindoles in good to excellent yield and enantioselectivity.

AB - The bifunctional quinine-derived thiourea catalyst 14 was found to catalyze the direct amination of unprotected 3-aryl and aliphatic substituted oxindoles with di-tert-butyl azodicarboxylate (DBAD) to construct a tetrasubstituted stereogenic carbon center at the C-3 position of oxindoles in good to excellent yield and enantioselectivity.

KW - 3-aminooxindoles

KW - asymmetric catalysis

KW - atom efficiency

KW - organocatalysis

KW - tetrasubstituted stereogenic carbon centers

UR - https://www.scopus.com/pages/publications/81555215435

U2 - 10.1002/adsc.201100379

DO - 10.1002/adsc.201100379

M3 - 文章

AN - SCOPUS:81555215435

SN - 1615-4150

VL - 353

SP - 2945

EP - 2952

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 16

ER -

Organocatalytic asymmetric α-amination of unprotected 3-aryl and 3-aliphatic substituted oxindoles using di-tert-butyl azodicarboxylate

Abstract

Keywords

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