Catalytic Asymmetric Synthesis of 2,2-Disubstituted Oxetanes from Ketones by Using a One-Pot Sequential Addition of Sulfur Ylide

被引:61
作者
Sone, Toshihiko [1 ]
Lu, Gang [1 ]
Matsunaga, Shigeki [1 ]
Shibasaki, Masakatsu [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
关键词
asymmetric synthesis; homogeneous catalysis; oxetanes; rare-earth metals; ylides; DIMETHYLOXOSULFONIUM METHYLIDE; KINETIC RESOLUTION; SUBSTITUTED OXETANES; EPOXIDE HYDROLASES; ACHIRAL ADDITIVES; COMPLEX; ENONES; POLYMERIZATION; OXIDATION; OLEFINS;
D O I
10.1002/anie.200805473
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Better the second time around: The title compounds were synthesized by using a one-pot double methylene transfer catalyzed by a heterobimetallic La/Li complex. Chiral amplification in the second step was the key to obtaining oxetanes in high enantiomeric excess (see scheme). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1677 / 1680
页数:4
相关论文
共 50 条
[1]   Catalytic, asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds: Scope, selectivity, and applications in synthesis [J].
Aggarwal, VK ;
Winn, CL .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :611-620
[2]   Synthetic applications of epoxide hydrolases [J].
Archelas, A ;
Furstoss, R .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2001, 5 (02) :112-119
[3]  
BERTOLINI F, 2008, J ORG CHEM
[4]   A critical outlook and comparison of enantioselective oxidation methodologies of olefins [J].
Bonini, C ;
Righi, G .
TETRAHEDRON, 2002, 58 (25) :4981-5021
[5]   Cationic ring-opening polymerization of oxetane via a non-steady-state controlled polymerization process: A comparison of initiators yielding living and nonliving polymers [J].
Bouchekif, Hassen ;
Philbin, Marcia I. ;
Colclough, Eamon ;
Amass, Allan J. .
MACROMOLECULES, 2008, 41 (06) :1989-1995
[6]   DIMETHYLOXOSULFONIUM METHYLIDE ((CH3)2SOCH2) AND DIMETHYLSULFONIUM METHYLIDE ((CH3)2SCH2) FORMATION AND APPLICATION TO ORGANIC SYNTHESIS [J].
COREY, EJ ;
CHAYKOVSKY, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) :1353-+
[7]   Hybrid free radical/cationic frontal photopolymerizations [J].
Crivello, James V. .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2007, 45 (18) :4331-4340
[8]   Remarkable ligand effect on the enantioselectivity of the chiral lanthanum complex-catalyzed asymmetric epoxidation of enones [J].
Daikai, K ;
Kamaura, M ;
Inanaga, J .
TETRAHEDRON LETTERS, 1998, 39 (40) :7321-7322
[9]   Opening of substituted oxetanes with H2O2 and alkyl hydroperoxides:: Stereoselective approach to 3-peroxyalcohols and 1,2,4-trioxepanes [J].
Dussault, PH ;
Trullinger, TK ;
Noor-e-Ain, F .
ORGANIC LETTERS, 2002, 4 (26) :4591-4593
[10]   Catalytic asymmetric epoxidation of α,β-unsaturated phosphane oxides with a Y(O-iPr)3/biphenyldiol complex [J].
Hara, Keiichi ;
Park, So-Young ;
Yamagiwa, Noriyuki ;
Matsunaga, Shigeki ;
Shibasaki, Masakatsu .
CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (8-9) :1500-1504