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

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 23期

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

页码：4025 / 4028

页数：4

共 27 条

[1] A facile three-step synthesis of 1,2-amino alcohols using the Ellman homochiral tert-butylsulfinamide [J].

Barrow, JC ;

Ngo, PL ;

Pellicore, JM ;

Selnick, HG ;

Nantermet, PG .

TETRAHEDRON LETTERS, 2001, 42 (11) :2051-2054

[2] Asymmetric synthesis of pre-protected α,α-disubstituted amino acids from tert-butanesulfinyl ketimines [J].

Borg, G ;

Chino, M ;

Ellman, JA .

TETRAHEDRON LETTERS, 2001, 42 (08) :1433-1436

[3] One-pot asymmetric synthesis of tert-butanesulfinyl-protected amines from ketones by the in situ reduction of tert-butanesulfinyl ketimines [J].

Borg, G ;

Cogan, DA ;

Ellman, JA .

TETRAHEDRON LETTERS, 1999, 40 (37) :6709-6712

[4] THE PHARMACOLOGY OF SIBUTRAMINE HYDROCHLORIDE (BTS54524), A NEW ANTIDEPRESSANT WHICH INDUCES RAPID NORADRENERGIC DOWN-REGULATION [J].

BUCKETT, WR ;

THOMAS, PC ;

LUSCOMBE, GP .

PROGRESS IN NEURO-PSYCHOPHARMACOLOGY & BIOLOGICAL PSYCHIATRY, 1988, 12 (05) :575-584

[5] Asymmetric synthesis of chiral amines by highly diastereoselective 1,2-additions of organometallic reagents to N-tert-butanesulfinyl imines [J].

Cogan, DA ;

Liu, GC ;

Ellman, J .

TETRAHEDRON, 1999, 55 (29) :8883-8904

[6] Asymmetric synthesis and properties of sulfinimines (thiooxime S-oxides) [J].

Davis, FA ;

Reddy, RE ;

Szewczyk, JM ;

Reddy, GV ;

Portonovo, PS ;

Zhang, HM ;

Fanelli, D ;

Reddy, RT ;

Zhou, P ;

Carroll, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2555-2563

[7] Concise asymmetric synthesis of α-amino acid derivatives from N-sulfinylimino esters [J].

Davis, FA ;

McCoull, W .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3396-3397

[8]

Davis FA, 1998, CHEM SOC REV, V27, P13

[9] ASYMMETRIC-SYNTHESIS OF SULFINIMINES - CHIRAL AMMONIA IMINE SYNTHONS [J].

DAVIS, FA ;

REDDY, RE ;

SZEWCZYK, JM ;

PORTONOVO, PS .

TETRAHEDRON LETTERS, 1993, 34 (39) :6229-6232

[10] Applications of the sulfinimine-mediated asymmetric strecker synthesis to the synthesis of α-alkyl α-amino acids [J].

Davis, FA ;

Lee, S ;

Zhang, HM ;

Fanelli, DL .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (25) :8704-8708

← 1 2 3 →