Copper phosphoramidite catalyzed enantioselective ring-opening of oxabicyclic alkenes: Remarkable reversal of stereocontrol

被引：126
|
作者：
Bertozzi, F
Pineschi, M
Macchia, F
Arnold, LA
Minnaard, AJ
Feringa, BL
机构：
[1] Univ Pisa, Dipartimento Chim Bioorgan & Biofarm, I-56126 Pisa, Italy
[2] Univ Groningen, Stratingh Inst, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands
来源：
ORGANIC LETTERS | 2002年 / 4卷 / 16期
关键词：
D O I：
10.1021/ol026220u
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] An unprecedented copper phosphoramidite catalyzed enantioselective alkylative ring-opening reaction of oxabenzonorbornadiene derivatives with dialkylzinc reagents is reported. The reaction shows high levels of ant stereoselectlvity (up to anti/syn >99:1), complementary to the Pd(0)-catalyzed syn-selective ring-opening protocol, allowing a new entry to anti-dihydronaphthols with high enantioselectivity (up to 99% ee).
引用
收藏
页码：2703 / 2705
页数：3
相关论文
共 50 条
  • [21] Rhodium-catalyzed asymmetric ring opening of oxabicyclic alkenes with phenols
    Lautens, M
    Fagnou, K
    Taylor, M
    ORGANIC LETTERS, 2000, 2 (12) : 1677 - 1679
  • [22] Mechanism, reactivity, and regioselectivity in rhodium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes: a DFT Investigation
    Zheng-Hang Qi
    Yi Zhang
    Yun Gao
    Ye Zhang
    Xing-Wang Wang
    Yong Wang
    Scientific Reports, 7
  • [23] Mechanism, reactivity, and regioselectivity in rhodium-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes: a DFT Investigation
    Qi, Zheng-Hang
    Zhang, Yi
    Gao, Yun
    Zhang, Ye
    Wang, Xing-Wang
    Wang, Yong
    SCIENTIFIC REPORTS, 2017, 7
  • [24] Asymmetric ring-opening reaction of oxabicyclic alkenes with aryl boronic acids catalyzed by p-containing palladacycles
    Zhang, Ting-Ke
    Mo, Dong-Liang
    Dai, Li-Xin
    Hou, Xue-Long
    ORGANIC LETTERS, 2008, 10 (17) : 3689 - 3692
  • [25] Mechanistic studies of the palladium-catalyzed ring opening of oxabicyclic alkenes with dialkylzinc
    Lautens, M
    Hiebert, S
    Renaud, JL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (28) : 6834 - 6839
  • [26] THE REDUCTIVE RING-OPENING OF OXABICYCLIC COMPOUNDS
    LAUTENS, M
    CHIU, P
    TETRAHEDRON LETTERS, 1991, 32 (37) : 4827 - 4830
  • [27] Rhodium-Catalyzed Enantioselective Synthesis of Oxazinones via an Asymmetric Ring Opening-Lactonization Cascade of Oxabicyclic Alkenes
    Yen, Andy
    Anh Hoang Pham
    Larin, Egor M.
    Lautens, Mark
    ORGANIC LETTERS, 2019, 21 (18) : 7549 - 7553
  • [28] Ring-opening reactions of oxabicyclic alkene compounds: enantioselective hydride and ethyl additions catalyzed by group 4 metals
    Millward, DB
    Sammis, G
    Waymouth, RM
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (13): : 3902 - 3909
  • [29] Rhodium-catalyzed asymmetric ring opening of oxabicyclic alkenes with organoboronic acids
    Lautens, M
    Dockendorff, C
    Fagnou, K
    Malicki, A
    ORGANIC LETTERS, 2002, 4 (08) : 1311 - 1314
  • [30] Rhodium-catalyzed asymmetric ring opening of oxabicyclic alkenes with sulfur nucleophiles
    Leong, P
    Lautens, M
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (06): : 2194 - 2196
12345