Rhodium-catalysed diastereo- and enantio-selective cyclopropanation of α-boryl styrenes

被引：8
|
作者：
Sun, Xiao [1 ]
Gu, Peiming [1 ]
Qin, Jiao [1 ]
Su, Yan [1 ]
机构：
[1] Ningxia Univ, Coll Chem & Chem Engn, State Key Lab High Efficiency Utilizat Coal & Gre, Yinchuan 750021, Ningxia, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2020年 / 56卷 / 82期
基金：
中国国家自然科学基金;
关键词：
C-H BORYLATION; ENANTIOSELECTIVE HYDROBORATION; COPPER(I)-CATALYZED REACTION; BUILDING-BLOCKS; ESTERS; ACID; DERIVATIVES; ALKENES; ANTIDEPRESSANT; STRATEGIES;
D O I：
10.1039/d0cc02549f
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A rhodium-catalyzed diastereo- and enantio-selective cyclopropanation of alpha-boryl styrenes with alpha-diazoarylacetates was established. Rh-2(S-PTTL)(4)(0.2 mol%) was found to be effective for the conversion, and 21 diastereopure cyclopropylboronates were prepared in high yields with excellent enantioselectivity (ee up to 99%).
引用
收藏
页码：12379 / 12382
页数：4
相关论文
共 42 条
  • [1] Highly regio- and enantio-selective rhodium-catalysed asymmetric hydroformylation without organic solvents
    Franciò, G
    Leitner, W
    CHEMICAL COMMUNICATIONS, 1999, (17) : 1663 - 1664
  • [2] Copper(I)/SaBOX catalyzed highly diastereo- and enantio-selective cyclopropanation of cis-1,2-disubstituted olefins with α-nitrodiazoacetates
    Feng, Liang-Wen
    Wang, Peng
    Wang, Lijia
    Tang, Yong
    SCIENCE BULLETIN, 2015, 60 (02) : 210 - 215
  • [3] Organo-catalyzed highly diastereo- and enantio-selective direct aldol reactions in water
    Zhao, Jun-Feng
    He, Long
    Jiang, Jun
    Tang, Zhuo
    Cun, Lin-Feng
    Gong, Liu-Zhu
    TETRAHEDRON LETTERS, 2008, 49 (21) : 3372 - 3375
  • [4] Copper(I)-catalyzed diastereo- and enantio-selective construction of optically pure exocyclic allenes
    Cheng-Yu He
    Yun-Xuan Tan
    Xin Wang
    Rui Ding
    Yi-Fan Wang
    Feng Wang
    Dingding Gao
    Ping Tian
    Guo-Qiang Lin
    Nature Communications, 11
  • [5] Diastereo- and enantio-selective crotylation of α-ketoesters using crotyl boronic acid ester complexes
    Chen, YP
    Eltepu, L
    Wentworth, P
    TETRAHEDRON LETTERS, 2004, 45 (45) : 8285 - 8288
  • [6] Copper(I)-catalyzed diastereo- and enantio-selective construction of optically pure exocyclic allenes
    He, Cheng-Yu
    Tan, Yun-Xuan
    Wang, Xin
    Ding, Rui
    Wang, Yi-Fan
    Wang, Feng
    Gao, Dingding
    Tian, Ping
    Lin, Guo-Qiang
    NATURE COMMUNICATIONS, 2020, 11 (01)
  • [7] Highly diastereo- and enantio-selective epoxidation of secondary allylic alcohols catalyzed by styrene monooxygenase
    Lin, Hui
    Liu, Yan
    Wu, Zhong-Liu
    CHEMICAL COMMUNICATIONS, 2011, 47 (09) : 2610 - 2612
  • [8] ENANTIO-SELECTIVE AND DIASTEREO-SELECTIVE SYNTHESIS OF SPIROCYCLIC COMPOUNDS
    SUEMUNE, H
    MAEDA, K
    KATO, K
    SAKAI, K
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (23): : 3441 - 3447
  • [9] Effect of counter-cations on aggregation and chiral discrimination: Application to highly diastereo- and enantio-selective syntheses
    Solladie-Cavallo, A
    ENANTIOMER, 1999, 4 (3-4): : 173 - 182
  • [10] ENANTIO-SELECTIVE AND DIASTEREO-SELECTIVE SYNTHESIS OF CARBOCYCLIC OXETANOCIN ANALOGS
    ICHIKAWA, Y
    NARITA, A
    SHIOZAWA, A
    HAYASHI, Y
    NARASAKA, K
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (24) : 1919 - 1921
12345