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Copper-Catalyzed Asymmetric Protoboration of β-Amidoacrylonitriles and β-Amidoacrylate Esters: An Efficient Approach to Functionalized Chiral α-Amino Boronate Esters
被引:34
作者:

Chen, Lili
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机构:
Chinese Acad Sci, Lanzhou Inst Chem Phys, Suzhou Res Inst, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
Univ Chinese Acad Sci, Beijing 100049, Peoples R China Chinese Acad Sci, Lanzhou Inst Chem Phys, Suzhou Res Inst, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

Zou, Xiaoliang
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Chinese Acad Sci, Lanzhou Inst Chem Phys, Suzhou Res Inst, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China Chinese Acad Sci, Lanzhou Inst Chem Phys, Suzhou Res Inst, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

Zhao, Haonan
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机构:
Chinese Acad Sci, Lanzhou Inst Chem Phys, Suzhou Res Inst, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China Chinese Acad Sci, Lanzhou Inst Chem Phys, Suzhou Res Inst, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China

Xu, Senmiao
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机构:
Chinese Acad Sci, Lanzhou Inst Chem Phys, Suzhou Res Inst, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China Chinese Acad Sci, Lanzhou Inst Chem Phys, Suzhou Res Inst, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
机构:
[1] Chinese Acad Sci, Lanzhou Inst Chem Phys, Suzhou Res Inst, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
基金:
中国国家自然科学基金;
关键词:
ALPHA;
BETA-UNSATURATED CARBONYL-COMPOUNDS;
CONJUGATE ADDITION;
ACID-DERIVATIVES;
ENANTIOSELECTIVE SYNTHESIS;
PINACOLBORYL ADDITION;
HYDROBORATION;
BORATION;
BORYLATION;
INVERSION;
CHEMISTRY;
D O I:
10.1021/acs.orglett.7b01740
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
A copper-catalyzed asymmetric protoboration of both Z-beta-amidoacrylonitriles and ethyl E-beta-amidoacrylates using bis(pinacolato)diboron has been developed for the first time. The process tolerates a vast array of substrates, delivering a series of stable functionalized chiral alpha-amino boronate esters in good yields and enantioselectivities under mild reaction conditions. The current method is also applicable for gram-scale synthesis without erosion of enantioselectivity. This work provides an attractive and complementary approach to synthesizing enantioriched chiral alpha-amino boronate esters.
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页码:3676 / 3679
页数:4
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