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 [1 ,2 ]
Zou, Xiaoliang [1 ]
Zhao, Haonan [1 ]
Xu, Senmiao [1 ]
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.
引用
收藏
页码:3676 / 3679
页数:4
相关论文
共 71 条
[1]   Development of the proteasome inhihitor Veleade™ (Bortezomib) [J].
Adams, J ;
Kauffman, M .
CANCER INVESTIGATION, 2004, 22 (02) :304-311
[2]   Synthesis of α-aminoboronic acids [J].
Andres, Patricia ;
Ballano, Gema ;
Calaza, M. Isabel ;
Cativiela, Carlos .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (08) :2291-2307
[3]   Inversion or Retention? Effects of Acidic Additives on the Stereochemical Course in Enantiospecific Suzuki-Miyaura Coupling of α-(Acetylamino)benzylboronic Esters [J].
Awano, Tomotsugu ;
Ohmura, Toshimichi ;
Suginome, Michinori .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (51) :20738-20741
[4]   Asymmetric copper-catalyzed synthesis of α-amino boronate esters from N-tert-butanesulfinyl aldimines [J].
Beenen, Melissa A. ;
An, Chihui ;
Ellman, Jonathan A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (22) :6910-+
[5]   Convergent, asymmetric synthesis of vicinal amino alcohols via Rh-catalyzed addition of α-amido trifluoroborates to carbonyls [J].
Buesking, Andrew W. ;
Ellman, Jonathan A. .
CHEMICAL SCIENCE, 2014, 5 (05) :1983-1987
[6]   Asymmetric Synthesis of Protected α-Amino Boronic Acid Derivatives with an Air- and Moisture-Stable Cu(II) Catalyst [J].
Buesking, Andrew W. ;
Bacauanu, Vlad ;
Cai, Irene ;
Ellman, Jonathan A. .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (08) :3671-3677
[7]   A new access to α-hydroxy boronic esters from α-alkoxyorganolithium reagents [J].
Carmès, L ;
Carreaux, F ;
Carboni, B ;
Mortier, J .
TETRAHEDRON LETTERS, 1998, 39 (07) :555-556
[8]   The development of enantioselective rhodium-catalysed hydroboration of olefins [J].
Carroll, AM ;
O'Sullivan, TP ;
Guiry, PJ .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (05) :609-631
[9]   Click Chemistry in Lead Optimization of Boronic Acids as β-Lactamase Inhibitors [J].
Caselli, Emilia ;
Romagnoli, Chiara ;
Vahabi, Roza ;
Taracila, Magdalena A. ;
Bonomo, Robert A. ;
Prati, Fabio .
JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (14) :5445-5458
[10]   Copper-Catalyzed Conjugate Addition of Diboron Reagents to α,β-Unsaturated Amides: Highly Reactive Copper-1,2-Bis(diphenylphosphino)benzene Catalyst System [J].
Chea, Heesung ;
Sim, Hak-Suk ;
Yun, Jaesook .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (06) :855-858