Carbene-catalyzed activation of cyclopropylcarbaldehydes for mannich reaction and δ-lactam formation: remote enantioselecitvity control and dynamic kinetic asymmetric transformation

Jie Lv; Jun Xu; Xuling Pan; Zhichao Jin; Yonggui Robin Chi

doi:10.1007/s11426-021-9989-1

Carbene-catalyzed activation of cyclopropylcarbaldehydes for mannich reaction and δ-lactam formation: remote enantioselecitvity control and dynamic kinetic asymmetric transformation

Jie Lv, Jun Xu, Xuling Pan, Zhichao Jin, Yonggui Robin Chi^*

^*Corresponding author for this work

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

28 Citations (Scopus)

Abstract

An N-heterocyclic carbene (NHC)-catalyzed enantioselective Mannich reaction of the remote γ-carbon of cyclopropylcarbaldehydes is disclosed for the first time. Diastereo- and enantiomerically enriched multicyclic δ-lactam compound is afforded as the main product from 8 possible stereo-specific isomers through dynamic kinetic asymmetric transformation (DYKAT) processes. Multiple chiral functional molecules can be afforded from the lactam products through simple protocols with retentions of the optical purities. [Figure not available: see fulltext.].

Original language	English
Pages (from-to)	985-990
Number of pages	6
Journal	Science China Chemistry
Volume	64
Issue number	6
DOIs	https://doi.org/10.1007/s11426-021-9989-1
Publication status	Published - Jun 2021
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2021, Science China Press and Springer-Verlag GmbH Germany, part of Springer Nature.

ASJC Scopus Subject Areas

General Chemistry

Keywords

1-cyclopropylcarbaldehydes
asymmetric reactions
dynamic kinetic asymmetric transformation
N-heterocyclic carbene
organocatalysis

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10.1007/s11426-021-9989-1

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title = "Carbene-catalyzed activation of cyclopropylcarbaldehydes for mannich reaction and δ-lactam formation: remote enantioselecitvity control and dynamic kinetic asymmetric transformation",

abstract = "An N-heterocyclic carbene (NHC)-catalyzed enantioselective Mannich reaction of the remote γ-carbon of cyclopropylcarbaldehydes is disclosed for the first time. Diastereo- and enantiomerically enriched multicyclic δ-lactam compound is afforded as the main product from 8 possible stereo-specific isomers through dynamic kinetic asymmetric transformation (DYKAT) processes. Multiple chiral functional molecules can be afforded from the lactam products through simple protocols with retentions of the optical purities. [Figure not available: see fulltext.].",

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author = "Jie Lv and Jun Xu and Xuling Pan and Zhichao Jin and Chi, {Yonggui Robin}",

note = "Publisher Copyright: {\textcopyright} 2021, Science China Press and Springer-Verlag GmbH Germany, part of Springer Nature.",

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doi = "10.1007/s11426-021-9989-1",

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T1 - Carbene-catalyzed activation of cyclopropylcarbaldehydes for mannich reaction and δ-lactam formation

T2 - remote enantioselecitvity control and dynamic kinetic asymmetric transformation

AU - Lv, Jie

AU - Xu, Jun

AU - Pan, Xuling

AU - Jin, Zhichao

AU - Chi, Yonggui Robin

PY - 2021/6

Y1 - 2021/6

N2 - An N-heterocyclic carbene (NHC)-catalyzed enantioselective Mannich reaction of the remote γ-carbon of cyclopropylcarbaldehydes is disclosed for the first time. Diastereo- and enantiomerically enriched multicyclic δ-lactam compound is afforded as the main product from 8 possible stereo-specific isomers through dynamic kinetic asymmetric transformation (DYKAT) processes. Multiple chiral functional molecules can be afforded from the lactam products through simple protocols with retentions of the optical purities. [Figure not available: see fulltext.].

AB - An N-heterocyclic carbene (NHC)-catalyzed enantioselective Mannich reaction of the remote γ-carbon of cyclopropylcarbaldehydes is disclosed for the first time. Diastereo- and enantiomerically enriched multicyclic δ-lactam compound is afforded as the main product from 8 possible stereo-specific isomers through dynamic kinetic asymmetric transformation (DYKAT) processes. Multiple chiral functional molecules can be afforded from the lactam products through simple protocols with retentions of the optical purities. [Figure not available: see fulltext.].

KW - 1-cyclopropylcarbaldehydes

KW - asymmetric reactions

KW - dynamic kinetic asymmetric transformation

KW - N-heterocyclic carbene

KW - organocatalysis

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Carbene-catalyzed activation of cyclopropylcarbaldehydes for mannich reaction and δ-lactam formation: remote enantioselecitvity control and dynamic kinetic asymmetric transformation

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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