Highly enantioselective addition of enals to isatin-derived ketimines catalyzed by N-heterocyclic carbenes: Synthesis of spirocyclic γ-lactams

Hui Lv; Bhoopendra Tiwari; Junming Mo; Chong Xing; Yonggui Robin Chi

doi:10.1021/ol302475g

Highly enantioselective addition of enals to isatin-derived ketimines catalyzed by N-heterocyclic carbenes: Synthesis of spirocyclic γ-lactams

Hui Lv, Bhoopendra Tiwari, Junming Mo, Chong Xing, Yonggui Robin Chi^*

^*Corresponding author for this work

Nanyang Technological University

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

187 Citations (Scopus)

Abstract

An N-heterocyclic carbene (NHC)-catalyzed annulation reaction of isatin N-Boc ketimines and enals is developed for the synthesis of spirocyclic oxindole-γ-lactams bearing one quaternary chiral center in good yields and excellent stereoselectivities (up to >20:1 dr and 99% ee).

Original language	English
Pages (from-to)	5412-5415
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	21
DOIs	https://doi.org/10.1021/ol302475g
Publication status	Published - Nov 2 2012
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol302475g

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title = "Highly enantioselective addition of enals to isatin-derived ketimines catalyzed by N-heterocyclic carbenes: Synthesis of spirocyclic γ-lactams",

abstract = "An N-heterocyclic carbene (NHC)-catalyzed annulation reaction of isatin N-Boc ketimines and enals is developed for the synthesis of spirocyclic oxindole-γ-lactams bearing one quaternary chiral center in good yields and excellent stereoselectivities (up to >20:1 dr and 99% ee).",

author = "Hui Lv and Bhoopendra Tiwari and Junming Mo and Chong Xing and Chi, {Yonggui Robin}",

year = "2012",

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doi = "10.1021/ol302475g",

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journal = "Organic Letters",

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T1 - Highly enantioselective addition of enals to isatin-derived ketimines catalyzed by N-heterocyclic carbenes

T2 - Synthesis of spirocyclic γ-lactams

AU - Lv, Hui

AU - Tiwari, Bhoopendra

AU - Mo, Junming

AU - Xing, Chong

AU - Chi, Yonggui Robin

PY - 2012/11/2

Y1 - 2012/11/2

N2 - An N-heterocyclic carbene (NHC)-catalyzed annulation reaction of isatin N-Boc ketimines and enals is developed for the synthesis of spirocyclic oxindole-γ-lactams bearing one quaternary chiral center in good yields and excellent stereoselectivities (up to >20:1 dr and 99% ee).

AB - An N-heterocyclic carbene (NHC)-catalyzed annulation reaction of isatin N-Boc ketimines and enals is developed for the synthesis of spirocyclic oxindole-γ-lactams bearing one quaternary chiral center in good yields and excellent stereoselectivities (up to >20:1 dr and 99% ee).

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U2 - 10.1021/ol302475g

DO - 10.1021/ol302475g

M3 - Article

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SN - 1523-7060

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JF - Organic Letters

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ER -

Highly enantioselective addition of enals to isatin-derived ketimines catalyzed by N-heterocyclic carbenes: Synthesis of spirocyclic γ-lactams

Abstract

ASJC Scopus Subject Areas

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