A Highly Stereoselective Redox Isomerization-Reductive Deuteration Sequence of Propargyl Amines to α-Deuterated Amino Acids

Zhipeng Zhao; Hongrui Lin; Zheng Zhang; Xiaotong Gao; Congbin Ji; Jian Zhou; Feng Zhou

doi:10.1021/acs.orglett.3c03140

A Highly Stereoselective Redox Isomerization-Reductive Deuteration Sequence of Propargyl Amines to α-Deuterated Amino Acids

Zhipeng Zhao
, Hongrui Lin
, Zheng Zhang
, Xiaotong Gao
, Congbin Ji^*
, Jian Zhou
, Feng Zhou^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University
Chongqing University of Science and Technology
Shangrao Normal University
CAS - Shanghai Institute of Organic Chemistry

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

2 Scopus citations

Abstract

Herein, we report a Cu-catalyzed redox isomerization-reductive deuteration sequence, providing facile access to a range of α-deuterated amino acid esters featuring an Z-configured alkene moiety with high yields. The advantages of this sequence include mild conditions, broad substrate scope, and excellent stereoselectivity. This research also represents a rare example of the Z-selective redox isomerization of propargyl amines.

Original language	English
Pages (from-to)	7895-7899
Number of pages	5
Journal	Organic Letters
Volume	25
Issue number	43
DOIs	https://doi.org/10.1021/acs.orglett.3c03140
State	Published - 3 Nov 2023

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10.1021/acs.orglett.3c03140

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title = "A Highly Stereoselective Redox Isomerization-Reductive Deuteration Sequence of Propargyl Amines to α-Deuterated Amino Acids",

abstract = "Herein, we report a Cu-catalyzed redox isomerization-reductive deuteration sequence, providing facile access to a range of α-deuterated amino acid esters featuring an Z-configured alkene moiety with high yields. The advantages of this sequence include mild conditions, broad substrate scope, and excellent stereoselectivity. This research also represents a rare example of the Z-selective redox isomerization of propargyl amines.",

author = "Zhipeng Zhao and Hongrui Lin and Zheng Zhang and Xiaotong Gao and Congbin Ji and Jian Zhou and Feng Zhou",

note = "Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

year = "2023",

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T1 - A Highly Stereoselective Redox Isomerization-Reductive Deuteration Sequence of Propargyl Amines to α-Deuterated Amino Acids

AU - Zhao, Zhipeng

AU - Lin, Hongrui

AU - Zhang, Zheng

AU - Gao, Xiaotong

AU - Ji, Congbin

AU - Zhou, Jian

AU - Zhou, Feng

PY - 2023/11/3

Y1 - 2023/11/3

N2 - Herein, we report a Cu-catalyzed redox isomerization-reductive deuteration sequence, providing facile access to a range of α-deuterated amino acid esters featuring an Z-configured alkene moiety with high yields. The advantages of this sequence include mild conditions, broad substrate scope, and excellent stereoselectivity. This research also represents a rare example of the Z-selective redox isomerization of propargyl amines.

AB - Herein, we report a Cu-catalyzed redox isomerization-reductive deuteration sequence, providing facile access to a range of α-deuterated amino acid esters featuring an Z-configured alkene moiety with high yields. The advantages of this sequence include mild conditions, broad substrate scope, and excellent stereoselectivity. This research also represents a rare example of the Z-selective redox isomerization of propargyl amines.

UR - https://www.scopus.com/pages/publications/85176495421

U2 - 10.1021/acs.orglett.3c03140

DO - 10.1021/acs.orglett.3c03140

M3 - 文章

C2 - 37874766

AN - SCOPUS:85176495421

SN - 1523-7060

VL - 25

SP - 7895

EP - 7899

JO - Organic Letters

JF - Organic Letters

IS - 43

ER -

A Highly Stereoselective Redox Isomerization-Reductive Deuteration Sequence of Propargyl Amines to α-Deuterated Amino Acids

Abstract

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