Asymmetric synthesis of diarylmethylamines by diastereoselective addition of organometallic reagents to chiral N-tert-butanesulfinimines:: switchover of diastereofacial selectivity

被引：111

作者：

Plobeck, N ^{[1
]}

Powell, D ^{[1
]}

机构：

[1] AstraZeneca R&D Montreal, Dept Chem, St Laurent, PQ H4S 1Z9, Canada

来源：

TETRAHEDRON-ASYMMETRY | 2002年 / 13卷 / 03期

关键词：

D O I：

10.1016/S0957-4166(02)00099-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Diastereoselective addition of organometallic reagents to chiral N-tert-butanesulfinimines gave alkylated adducts in high yields and diastereoselectivities. Cleavage of the chiral auxiliary under mildly acidic conditions gave diarylmethylamines in high yield. A reversal in the diastereoselectivity was observed by using either phenylmagnesium bromide in toluene or phenyllithium in THF. The use of the same chiral auxiliary thus allowed the synthesis of both enantiomers of a number of diarylmethylamines. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：303 / 310

页数：8

共 10 条

[1] PROBES FOR NARCOTIC RECEPTOR-MEDIATED PHENOMENA .19. SYNTHESIS OF (+)-4-[(ALPHA-R)-ALPHA-((2S,5R)-4-ALLYL-2,5-DIMETHYL-1-PIPERAZINYL)-3-METHOXYBENZYL]-N,N-DIETHYLBENZAMIDE (SNC-80) - A HIGHLY SELECTIVE, NONPEPTIDE DELTA-OPIOID RECEPTOR AGONIST [J].

CALDERON, SN ;

ROTHMAN, RB ;

PORRECA, F ;

FLIPPENANDERSON, JL ;

MCNUTT, RW ;

XU, H ;

SMITH, LE ;

BILSKY, EJ ;

DAVIS, P ;

RICE, KC .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (14) :2125-2128

[2] 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

[3] Asymmetric synthesis of diarylmethylamines: preparation of selective opioid delta receptor ligands [J].

Delorme, D ;

Berthelette, C ;

Lavoie, R ;

Roberts, E .

TETRAHEDRON-ASYMMETRY, 1998, 9 (22) :3963-3966

[4] Switchover of diastereofacial selectivity in the condensation reaction of optically active N-sulfinimine with ester enolate [J].

Fujisawa, T ;

Kooriyama, Y ;

Shimizu, M .

TETRAHEDRON LETTERS, 1996, 37 (22) :3881-3884

[5] Rhodium-catalyzed asymmetric arylation of imines with organostannanes. Asymmetric synthesis of diarylmethylamines [J].

Hayashi, T ;

Ishigedani, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (05) :976-977

[6] Synthesis of enantiomerically pure N-tert-butanesulfinyl imines (tert-butanesulfinimines) by the direct condensation of tert-butanesulfinamide with aldehydes and ketones [J].

Liu, GC ;

Cogan, DA ;

Owens, TD ;

Tang, TP ;

Ellman, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1278-1284

[7] Complexation with barium(II) allows the inference of the absolute configuration of primary amines by NMR [J].

López, B ;

Quiñoá, E ;

Riguera, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) :9724-9725

[8] LEAD-TETRAACETATE CLEAVAGE OF CHIRAL PHENYLGLYCINOL DERIVED SECONDARY-AMINES WITHOUT RACEMIZATION [J].

MOKHALLALATI, MK ;

PRIDGEN, LN .

SYNTHETIC COMMUNICATIONS, 1993, 23 (14) :2055-2064

[9]

OPALKA CJ, 1995, SYNTHESIS-STUTTGART, V766, P768

[10] New diarylmethylpiperazines as potent and selective nonpeptidic δ opioid receptor agonists with increased in vitro metabolic stability [J].

Plobeck, N ;

Delorme, D ;

Wei, ZY ;

Yang, H ;

Zhou, F ;

Schwarz, P ;

Gawell, L ;

Gagnon, H ;

Pelcman, B ;

Schmidt, R ;

Yue, SY ;

Walpole, C ;

Brown, W ;

Zhou, E ;

Labarre, M ;

Payza, K ;

St-Onge, S ;

Kamassah, A ;

Morin, PE ;

Projean, D ;

Ducharme, J ;

Roberts, E .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (21) :3878-3894

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