Enantioselective Palladium-Catalyzed Carbozincation of Cyclopropenes

被引：74
|
作者：
Kraemer, Katja [1 ]
Leong, Paul [1 ]
Lautens, Mark [1 ]
机构：
[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 04期
基金：
加拿大自然科学与工程研究理事会;
关键词：
OXABICYCLIC ALKENES; GRIGNARD-REAGENTS; DERIVATIVES; CARBOMETALATION; CHEMISTRY; ADDITIONS;
D O I：
10.1021/ol1029904
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly enantioselective palladium-catalyzed carbozincation of cyclopropenes has been developed. The intermediate cyclopropylzinc species, after transmetalation with copper, were trapped with various electrophiles. This one-pot procedure furnished functionalizied cyclopropenes with excellent diastereo- and enantioselectivity.
引用
收藏
页码：819 / 821
页数：3
相关论文
共 50 条
  • [21] Palladium-catalyzed enantioselective synthesis of carbanucleosides
    Trost, BM
    Madsen, R
    Guile, SD
    Brown, B
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (25) : 5947 - 5956
  • [22] Palladium-catalyzed enantioselective organic transformations
    Tenaglia, A
    Heumann, A
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (15) : 2180 - 2184
  • [23] Palladium-catalyzed enantioselective Heine reaction
    Kennedy, Katlyn
    Punk, Molly
    Merkley, Charlotte
    Morgan, Jeremy
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
  • [24] Palladium-Catalyzed Enantioselective α-Arylation of α-Fluoroketones
    Jiao, Zhiwei
    Beiger, Jason J.
    Jin, Yushu
    Ge, Shaozhong
    Zhou, Jianrong Steve
    Hartwig, John F.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (49) : 15980 - 15986
  • [25] Palladium-Catalyzed Addition of Alkynes to Cyclopropenes: An Entry to Stereodefined Alkynylcyclopropanes
    Tenaglia, Alphonse
    Le Jeune, Karel
    Giordano, Laurent
    Buono, Gerard
    ORGANIC LETTERS, 2011, 13 (04) : 636 - 639
  • [26] Palladium-Catalyzed Living/Controlled Vinyl Addition Polymerization of Cyclopropenes
    Zhang, Zepeng
    Gao, Yunpeng
    Chen, Shufeng
    Wang, Jianbo
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (42) : 17806 - 17815
  • [27] Palladium-Catalyzed Enantioselective Heteroarenyne Cycloisomerization Reaction
    Zhao, Ping
    Luan, Xinjun
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (06) : 2520 - 2521
  • [28] Photoinduced Palladium-Catalyzed Enantioselective Cascade Dearomatization
    Zhang Ying
    Huang Huan-Ming
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (06) : 2061 - 2062
  • [29] Enantioselective palladium-catalyzed diarylation of unactivated alkenes
    Ju, Baihang
    Chen, Shigui
    Kong, Wangqing
    CHEMICAL COMMUNICATIONS, 2019, 55 (95) : 14311 - 14314
  • [30] Enantioselective palladium-catalyzed decarboxylative allylic alkylations
    You, Shu-Li
    Dai, Li-Xin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (32) : 5246 - 5248
12345