Synthesis of Vinyl Boronates from Aldehydes by a Practical Boron-Wittig Reaction

被引:176
作者
Coombs, John R. [1 ]
Zhang, Liang [1 ]
Morken, James P. [1 ]
机构
[1] Boston Coll, Dept Chem, Merkert Chem Ctr, Chestnut Hill, MA 02467 USA
基金
美国国家卫生研究院;
关键词
OLEFIN CROSS-METATHESIS; CATALYZED ASYMMETRIC 1,4-ADDITION; TERMINAL ALKYNES; STEREOSELECTIVE-SYNTHESIS; HYDROBORATION REAGENT; CONVENIENT SYNTHESIS; CARBONYL-COMPOUNDS; COUPLING REACTIONS; INTERNAL ALKYNES; HIGHLY REGIO;
D O I
10.1021/acs.orglett.5b00480
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly stereoselective boron-Wittig reaction between stable and readily accessible 1,1-bis(pinacolboronates) and aldehydes furnishes a variety of synthetically useful di- and trisubstituted vinyl boronate esters.
引用
收藏
页码:1708 / 1711
页数:4
相关论文
共 56 条
[1]   TOTAL SYNTHESIS OF A FULLY PROTECTED PALYTOXIN CARBOXYLIC-ACID [J].
ARMSTRONG, RW ;
BEAU, JM ;
CHEON, SH ;
CHRIST, WJ ;
FUJIOKA, H ;
HAM, WH ;
HAWKINS, LD ;
JIN, H ;
KANG, SH ;
KISHI, Y ;
MARTINELLI, MJ ;
MCWHORTER, WW ;
MIZUNO, M ;
NAKATA, M ;
STUTZ, AE ;
TALAMAS, FX ;
TANIGUCHI, M ;
TINO, JA ;
UEDA, K ;
UENISHI, J ;
WHITE, JB ;
YONAGA, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (19) :7525-7530
[2]   Recent developments in alkyne borylations [J].
Barbeyron, Renaud ;
Benedetti, Erica ;
Cossy, Janine ;
Vasseur, Jean-Jacques ;
Arseniyadis, Stellios ;
Smietana, Michael .
TETRAHEDRON, 2014, 70 (45) :8431-8452
[3]   New approaches to olefin cross-metathesis [J].
Blackwell, HE ;
O'Leary, DJ ;
Chatterjee, AK ;
Washenfelder, RA ;
Bussmann, DA ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (01) :58-71
[4]  
Brown H.C., 1981, ALDRICHIM ACTA, V14, P3
[6]   HYDROBORATION .39. 1,3,2-BENZODIOXABOROLE (CATECHOLBORANE) AS A NEW HYDROBORATION REAGENT FOR ALKENES AND ALKYNES - GENERAL SYNTHESIS OF ALKANEBORONIC AND ALKENEBORONIC ACIDS AND ESTERS VIA HYDROBORATION - DIRECTIVE EFFECTS IN HYDROBORATION OF ALKENES AND ALKYNES WITH CATECHOLBORANE [J].
BROWN, HC ;
GUPTA, SK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (18) :5249-5255
[7]   Boronic Acids and Esters in the Petasis-Borono Mannich Multicomponent Reaction [J].
Candeias, Nuno R. ;
Montalbano, Francesco ;
Cal, Pedro M. S. D. ;
Gois, Pedro M. P. .
CHEMICAL REVIEWS, 2010, 110 (10) :6169-6193
[8]   Enantiomerically Enriched Tris(boronates): Readily Accessible Conjunctive Reagents for Asymmetric Synthesis [J].
Coombs, John R. ;
Zhang, Liang ;
Morken, James P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (46) :16140-16143
[9]   Recent developments in asymmetric multicomponent reactions [J].
de Graaff, Corien ;
Ruijter, Eelco ;
Orru, Romano V. A. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (10) :3969-4009
[10]   Stereoselective Synthesis of Allylsilanes Bearing Tetrasubstituted Olefin via 2,2-Diborylethylsilane [J].
Endo, Kohei ;
Sakamoto, Akira ;
Ohkubo, Takahiro ;
Shibata, Takanori .
CHEMISTRY LETTERS, 2011, 40 (12) :1440-1442