Reversal of diastereofacial selectivity in hydride reductions of N-tert-butanesulfinyl imines

被引：97

作者：

Colyer, John T. ^{[1
]}

Andersen, Neil G. ^{[1
]}

Tedrow, Jason S. ^{[1
]}

Soukup, Troy S. ^{[1
]}

Faul, Margaret M. ^{[1
]}

机构：

[1] Amgen Inc, Chem Proc Res & Dev, Thousand Oaks, CA 91320 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 18期

关键词：

D O I：

10.1021/jo0609834

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of N-tert-butanesulfinyl imines were reduced with NaBH4 in THF containing 2% water to provide the corresponding secondary sulfinamides in high yield and diastereoselectivity. By using the same sulfinyl imine starting materials and changing the reductant to L-Selectride, the stereoselectivity could be efficiently reversed to afford the opposite product diastereomer in high yield and selectivity.

引用

页码：6859 / 6862

页数：4

共 29 条

[1] Synthesis of (R)-(+)-methyl 3-amino-3-(5-hydroxy-2-pyridinyl)propanoate an analog of L-azatyrosine [J].

Adamczyk, M ;

Reddy, RE .

TETRAHEDRON-ASYMMETRY, 2001, 12 (07) :1047-1054

[2]

ANNUNZIATA R, 1982, J CHEMS OC P1, V1, P339

[3] 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

[4] 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

[5] BETA-ASYMMETRIC INDUCTION IN REDUCTION OF N-ALKYLIDENESULPHINAMIDES - SYNTHESIS OF OPTICALLY-ACTIVE AMINES [J].

CINQUINI, M ;

COZZI, F .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (20) :723-724

[6] 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

[7] 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

[8]

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

[9] Enantioselective synthesis of antiinfluenza compound A-315675 [J].

DeGoey, DA ;

Chen, HJ ;

Flosi, WJ ;

Grampovnik, DJ ;

Yeung, CM ;

Klein, LL ;

Kempf, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) :5445-5453

[10] Dual protein farnesyltransferase-geranylgeranyltransferase-I inhibitors as potential cancer chemotherapeutic agents [J].

DeSolms, SJ ;

Ciccarone, TM ;

MacTough, SC ;

Shaw, AW ;

Buser, CA ;

Ellis-Hutchings, M ;

Fernandes, C ;

Hamilton, KA ;

Huber, HE ;

Kohl, NE ;

Lobell, RB ;

Robinson, RG ;

Tsou, NN ;

Walsh, ES ;

Graham, SL ;

Beese, LS ;

Taylor, JS .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (14) :2973-2984

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