Properly designed modular asymmetric synthesis for enantiopure sulfinamide auxiliaries from N-sulfonyl-1,2,3-oxathiazolidine-2-oxide agents

被引:102
作者
Han, ZX [1 ]
Krishnamurthy, D [1 ]
Grover, P [1 ]
Fang, QK [1 ]
Senanayake, CH [1 ]
机构
[1] Sepracor Inc, Chem Proc Res & Dev, Marlborough, MA 01752 USA
关键词
D O I
10.1021/ja0200692
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Simple and practical asymmetric synthesis of functionally differentiated aminoindanol based endo-N-sulfonyl 1,2,3-oxathiazolidine-2-oxide as sulfinyl transfer agents are developed. The importance of these new and unique sulfinyl transfer reagents are exemplified by the expedient production of several sulfinamide ligands, including either enantiomer of (R)-tert-butanesulfinamide in excellent yields and enantiopurities. Copyright © 2002 American Chemical Society.
引用
收藏
页码:7880 / 7881
页数:2
相关论文
共 13 条
[1]   Catalytic asymmetric oxidation of tert-butyl disulfide.: Synthesis of tert-butanesulfinamides, tert-butyl sulfoxides, and tert-butanesulfinimines [J].
Cogan, DA ;
Liu, GC ;
Kim, KJ ;
Backes, BJ ;
Ellman, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (32) :8011-8019
[2]   Improved synthesis of enantiopure sulfinimines (thiooxime S-oxides) from p-toluenesulfinamide and aldehydes and ketones [J].
Davis, FA ;
Zhang, YL ;
Andemichael, Y ;
Fang, TA ;
Fanelli, DL ;
Zhang, HM .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1403-1406
[3]  
Davis FA, 1998, CHEM SOC REV, V27, P13
[4]  
Fanelli D. L., 1999, ORG SYNTH, V77, P50
[5]   First preparation of enantiomerically pure sibutramine and its major metabolite, and determination of their absolute configuration by single crystal X-ray analysis [J].
Fang, QK ;
Senanayake, CH ;
Han, ZX ;
Morency, C ;
Grover, P ;
Malone, RE ;
Bulter, H ;
Wald, SA ;
Cameron, TS .
TETRAHEDRON-ASYMMETRY, 1999, 10 (23) :4477-4480
[6]   Large-scale synthesis of enantio- and diastereomerically pure (R,R)-formoterol [J].
Hett, R ;
Fang, QK ;
Gao, Y ;
Wald, SA ;
Senanayake, CH .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1998, 2 (02) :96-99
[7]  
KAGAN HB, 1990, SYNLETT, P643
[8]   Catalytic asymmetric synthesis of tert-butanesulfinamide. Application to the asymmetric synthesis of amines [J].
Liu, GC ;
Cogan, DA ;
Ellman, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (41) :9913-9914
[9]   Synthesis, utility, and structure of novel bis(sulfinyl)imidoamidine ligands for asymmetric Lewis acid catalysis [J].
Owens, TD ;
Hollander, FJ ;
Oliver, AG ;
Ellman, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (07) :1539-1540
[10]   Asymmetric synthesis of cetirizine dihydrochloride [J].
Pflum, DA ;
Krishnamurthy, D ;
Han, ZX ;
Wald, SA ;
Senanayake, CH .
TETRAHEDRON LETTERS, 2002, 43 (06) :923-926