Asymmetric synthesis of syn- and anti-1,3-amino alcohols

被引：131

作者：

Kochi, T ^{[1
]}

Tang, TP ^{[1
]}

Ellman, JA ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Ctr New Direct Organ Synthesis, Berkeley, CA 94720 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 23期

关键词：

D O I：

10.1021/ja026292g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first application of metalloenamines derived from N-sulfinyl imines is reported for the highly diastereoselective addition to aldehydes. Reduction of the β-hydroxy-N-sulfinyl imine products with catecholborane and LiBHEt3 provides syn- and anti-1,3-amino alcohol derivatives, respectively, with very high diastereomeric ratios. Copyright © 2002 American Chemical Society.

引用

页码：6518 / 6519

页数：2

共 32 条

[1] Diastereospecific synthesis of enantiomerically pure polysubstituted azetidines from 1,3-amino alcohols with three chiral centers [J].

Barluenga, J ;

FernandezMari, F ;

Viado, AL ;

Aguilar, E ;

Olano, B .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5659-5662

[2] 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

[3] Epoxyalcohol route to hydroxyethylene dipeptide isosteres: a new synthesis of the diaminoalcohol core of HIV-protease inhibitor ABT-538 (Ritonavir) [J].

Benedetti, F ;

Norbedo, S .

CHEMICAL COMMUNICATIONS, 2001, (02) :203-204

[4]

BERGBREITER DE, 1984, ASYMMETRIC SYNTHESIS, V2, P243

[5] 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

[6] 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

[7] Synthesis of a potent wide-spectrum serotonin-, norepinephrine-, dopamine-reuptake inhibitor (SNDRI) and a species-selective dopamine-reuptake inhibitor based on the gamma-amino alcohol functional group [J].

Carlier, PR ;

Lo, MMC ;

Lo, PCK ;

Richelson, E ;

Tatsumi, M ;

Reynolds, IJ ;

Sharma, TA .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (05) :487-492

[8] Asymmetric synthesis of α,α-dibranched amines by the trimethylaluminum-mediated 1,2-addition of organolithiums to tert-butanesulfinyl ketimines [J].

Cogan, DA ;

Ellman, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (01) :268-269

[9] 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

[10] 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

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