First application of tunable alkyl or aryl sulfinamides to the stereoselective synthesis of a chiral amine:: Asymmetric synthesis of (R)-didesmethylsibutramine ((R)-DDMS) using (R)-triethylmethylsulfinamide ((R)-TESA)

被引:37
作者
Han, ZX [1 ]
Krishnamurthy, D [1 ]
Pflum, D [1 ]
Grover, P [1 ]
Wald, SA [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/ol026699q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] highly diastereoselective addition of i-BuLi to a triethylmethylsulfinamide derived aldimine was used as the key step in the first asymmetric synthesis of (R)-didesmethylsibutramine, a metabolite of sibutramine for the potential treatment of CNS disorders.
引用
收藏
页码:4025 / 4028
页数:4
相关论文
共 27 条
[21]   Asymmetric synthesis of diarylmethylamines by diastereoselective addition of organometallic reagents to chiral N-tert-butanesulfinimines:: switchover of diastereofacial selectivity [J].
Plobeck, N ;
Powell, D .
TETRAHEDRON-ASYMMETRY, 2002, 13 (03) :303-310
[22]   Asymmetric synthesis of trifluoromethylated allylic amines using α,β-unsaturated N-tert-butanesulfinimines [J].
Prakash, GKS ;
Mandal, M ;
Olah, GA .
ORGANIC LETTERS, 2001, 3 (18) :2847-2850
[23]  
Prakash GKS, 2001, ANGEW CHEM INT EDIT, V40, P589, DOI 10.1002/1521-3773(20010202)40:3<589::AID-ANIE589>3.0.CO
[24]  
2-9
[25]  
SENANAYAKE CH, 2001, Patent No. 0151453
[26]   Asymmetric synthesis of protected 1,2-amino alcohols using tert-butanesulfinyl aldimines and ketimines [J].
Tang, TP ;
Volkman, SK ;
Ellman, JA .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) :8772-8778
[27]  
Zhou P, 2000, ADV SULF CHEM, V2, P249