A MECHANISTICALLY DESIGNED MONO-CINCHONA ALKALOID IS AN EXCELLENT CATALYST FOR THE ENANTIOSELECTIVE DIHYDROXYLATION OF OLEFINS

被引：43
|
作者：
COREY, EJ
NOE, MC
GROGAN, MJ
机构：
[1] Department of Chemistry, Harvard University, Cambridge
来源：
TETRAHEDRON LETTERS | 1994年 / 35卷 / 35期
关键词：
D O I：
10.1016/S0040-4039(00)78237-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
On the basis of ideas recently advanced regarding the origin of enantioselectivity in the OsO4-promoted dihydroxylation of olefins catalyzed by bis-cinchona alkaloid derivatives such as 1, specifically strong evidence for reaction via transition stale assembly 2, the mono-quinidine derivative 3 was selected as a promising catalytic ligand. The experimental observation of high enantioselectivity promoted by 3 provides additional evidence in favor of transition-state 2.
引用
收藏
页码：6427 / 6430
页数：4
相关论文
共 50 条
  • [21] Enantioselective Hydrogenation of Trifluoromethylcyclohexyl Ketone on Cinchona Alkaloid Modified Pt-Alumina Catalyst
    Károly Felföldi
    Tibor Varga
    Péter Forgó
    Mihály Bartók
    Catalysis Letters, 2004, 97 : 65 - 70
  • [22] Enantioselective hydrogenation of trifluoromethylcyclohexyl ketone on cinchona alkaloid modified Pt-alumina catalyst
    Felföldi, K
    Varga, T
    Forgó, P
    Bartók, M
    CATALYSIS LETTERS, 2004, 97 (1-2) : 65 - 70
  • [23] Enantioselective Diels-Alder reaction of simple α,β-unsaturated ketones with a cinchona alkaloid catalyst
    Singh, Ravi P.
    Bartelson, Keith
    Wang, Yi
    Su, Heng
    Lu, Xiaojie
    Deng, Li
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (08) : 2422 - 2423
  • [24] RIGID AND HIGHLY ENANTIOSELECTIVE CATALYST FOR THE DIHYDROXYLATION OF OLEFINS USING OSMIUM TETRAOXIDE CLARIFIES THE ORIGIN OF ENANTIOSPECIFICITY
    COREY, EJ
    NOE, MC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (26) : 12579 - 12580
  • [25] OsO4•Streptavidin: A Tunable Hybrid Catalyst for the Enantioselective cis-Dihydroxylation of Olefins
    Koehler, Valentin
    Mao, Jincheng
    Heinisch, Tillmann
    Pordea, Anca
    Sardo, Alessia
    Wilson, Yvonne M.
    Knoerr, Livia
    Creus, Marc
    Prost, Jean-Christophe
    Schirmer, Tilman
    Ward, Thomas R.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (46) : 10863 - 10866
  • [26] Osmium-catalyzed asymmetric dihydroxylation of olefins by H2O2;: Dual role of the cinchona alkaloid ligand
    Jonsson, SY
    Adolfsson, H
    Bäckvall, JE
    ORGANIC LETTERS, 2001, 3 (22) : 3463 - 3466
  • [27] Cinchona alkaloid-Lewis acid catalyst systems for enantioselective ketene-aldehyde cycloadditions
    Zhu, C
    Shen, XQ
    Nelson, SG
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (17) : 5352 - 5353
  • [28] Cinchona Alkaloid-Lewis Acid Catalyst Systems for Enantioselective Ketene-Aldehyde Cycloadditions
    1600, American Chemical Society (126):
  • [29] MCM-41 Anchored Cinchona Alkaloid for Catalytic Asymmetric Dihydroxylation of Olefins: A Clean Protocol for Chiral Diols Using Molecular Oxygen
    Boyapati M. Choudary
    Naidu S. Chowdari
    Karangula Jyothi
    Mannepalli L. Kantam
    Catalysis Letters, 2002, 82 : 99 - 102
  • [30] MCM-41 anchored cinchona alkaloid for catalytic asymmetric dihydroxylation of olefins: a clean protocol for chiral diols using molecular oxygen
    Choudary, BM
    Chowdari, NS
    Jyothi, K
    Kantam, ML
    CATALYSIS LETTERS, 2002, 82 (1-2) : 99 - 102
12345