Catalytic asymmetric sulfimidation of 1,3-dithianes

被引:27
作者
Miyake, Y [1 ]
Takada, H [1 ]
Ohe, K [1 ]
Uemura, S [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Energy & Hydrocarbon Chem, Sakyo Ku, Kyoto 6068501, Japan
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 15期
关键词
D O I
10.1039/a802915f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
lA direct catalytic sulfimidation of l,3-dithianes to the corresponding chiral monosulfimides with N-(p-tolylsulfonyl)imino(phenyl)iodinane (TsN=IPh) using a catalytic amount of copper(I) triflate (CuOTf) and a chiral 4,4'-disubstituted bis(oxazoline) as ligand has been developed. The reaction affords the chiral monosulfimides in good yield and with moderate enantioselectivity (up to 40% ee).
引用
收藏
页码:2373 / 2376
页数:4
相关论文
共 23 条
[1]   ANION REACTIONS OF 1,3-DITHIANE 1,3-DIOXIDE WITH CARBONYL-COMPOUNDS - HIGH DIASTEREOSELECTIVITY WITH AROMATIC-ALDEHYDES UNDER CONDITIONS OF EQUILIBRIUM CONTROL [J].
AGGARWAL, VK ;
FRANKLIN, R ;
MADDOCK, J ;
EVANS, GR ;
THOMAS, A ;
MAHON, MF ;
MOLLOY, KC ;
RICE, MJ .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (07) :2174-2182
[2]   trans-1,3-dithiane-1,3-dioxide; a chiral acyl anion equivalent. Enantioselective synthesis of alpha-hydroxy- carboxylic acids, esters, amides and ketones [J].
Aggarwal, VK ;
Thomas, A ;
Schade, S .
TETRAHEDRON, 1997, 53 (48) :16213-16228
[3]   CHIRAL, BISFUNCTIONALIZATION OF SUBSTRATES - A POWERFUL STRATEGY FOR THE ASYMMETRIC-SYNTHESIS OF C2 SYMMETRIAL COMPOUNDS AND ITS APPLICATION TO THE SYNTHESIS OF ENANTIOMERICALLY PURE TRANS-1,3-DITHIANE 1,3-DIOXIDE [J].
AGGARWAL, VK ;
EVANS, G ;
MOYA, E ;
DOWDEN, J .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) :6390-6391
[4]   Chemistry of silyl thioketones .9. A new selective synthesis of 1-silyl-1-enethiols and of 2-silyl-thiacycloalk-2-enes of common to large ring size. [J].
Bonini, BF ;
ComesFranchini, M ;
Fochi, M ;
Mazzanti, G ;
Ricci, A .
TETRAHEDRON, 1996, 52 (13) :4803-4816
[5]   CONFORMATIONAL PREFERENCE OF S-N BOND IN THIAN AND 1,3-DITHIAN 1-IMIDES [J].
CLAUS, PK ;
VIERHAPPER, FW ;
WILLER, RL .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (24) :1002-1003
[6]   CONFORMATIONAL ANALYSIS .18. 1,3-DITHIANES . CONFORMATIONAL PREFERENCES OF ALKYL SUBSTITUENTS AND CHAIR-BOAT ENERGY DIFFERENCE [J].
ELIEL, EL ;
HUTCHINS, RO .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (10) :2703-&
[7]   CONFORMATIONAL PREFERENCES OF SULFIMIDES [J].
ERRINGTON, W ;
SPAREY, TJ ;
TAYLOR, PC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (07) :1439-1444
[8]  
GREENWALD RB, 1975, TETRAHEDRON LETT, P3885
[9]   STEREOELECTRONIC INTERPRETATION FOR THE ANOMALOUS H-1-NMR CHEMICAL-SHIFTS AND ONE-BOND C-H COUPLING-CONSTANTS (PERLIN EFFECTS) IN 1,3-DIOXANES, 1,3-OXATHIANES, AND 1,3-DITHIANES - SPECTROSCOPIC AND THEORETICAL OBSERVATIONS [J].
JUARISTI, E ;
CUEVAS, G ;
VELA, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :5796-5804
[10]   MECHANISM OF THE (DIIMINE)COPPER-CATALYZED ASYMMETRIC AZIRIDINATION OF ALKENES - NITRENE TRANSFER VIA LIGAND-ACCELERATED CATALYSIS [J].
LI, Z ;
QUAN, RW ;
JACOBSEN, EN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (21) :5889-5890