Following an ISES lead: The first examples of asymmetric Ni(0)-mediated allylic amination

被引：63

作者：

Berkowitz, DB ^{[1
]}

Maiti, G ^{[1
]}

机构：

[1] Univ Nebraska, Dept Chem, Lincoln, NE 68588 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 16期

关键词：

D O I：

10.1021/ol049159x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An ISES (in situ enzymatic screening) lead pointed to conditions (PMP N-protecting group, Ni(cod)(2) catalyst precursor) under which chiral, bidentate phosphines could promote Ni(0)-mediated allylic amination. Therefore, bidentate phosphines bearing central, axial, and planar chirality were examined with two model substrates of interest for PLP-enzyme inhibitor synthesis. In the best case, with (R)-MeO-BIPHEP, vinylglycinol derivative 2 was obtained in 75% ee (97% ee, one recrystallization) from 1. Further manipulation provided a Ni(0)-mediated entry into L-Vinylglycine.

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页码：2661 / 2664

页数：4

相关论文

共 59 条

[1] Enantioselective synthesis of (S)-Vigabatrin(R) [J].

Alcon, M ;

Poch, M ;

Moyano, A ;

Pericas, MA ;

Riera, A .

TETRAHEDRON-ASYMMETRY, 1997, 8 (17) :2967-2974

[2] Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity [J].

Anderson, CE ;

Overman, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (41) :12412-12413

[3] DEAMINATION AND GAMMA-ADDITION REACTIONS OF VINYLGLYCINE CATALYZED BY YEAST KYNURENINE AMINOTRANSFERASE, AND SUICIDAL INACTIVATION OF THE ENZYME DURING ITS PROCESSING [J].

ASADA, Y ;

TANIZAWA, K ;

YONAHA, K ;

SODA, K .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1988, 52 (11) :2873-2878

[4] Preparation and synthetic applications of (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals:: Asymmetric synthesis of (S)- and (R)-2-amino-2-methylbutanoic acids (Iva) [J].

Avenoza, A ;

Cativiela, C ;

Corzana, F ;

Peregrina, JM ;

Zurbano, MM .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (22) :8220-8225

[5]

Badorrey R, 1997, SYNTHESIS-STUTTGART, P747

[6] 1,3-DIPHENYLALLYL COMPLEXES OF PALLADIUM(II) - NMR, X-RAY, AND CATALYTIC STUDIES [J].

BARBARO, P ;

PREGOSIN, PS ;

SALZMANN, R ;

ALBINATI, A ;

KUNZ, RW .

ORGANOMETALLICS, 1995, 14 (11) :5160-5170

[7]

Bartels B, 2002, EUR J INORG CHEM, P2569

[8] THE FREE-RADICAL CHEMISTRY OF CARBOXYLIC ESTERS OF 2-SELENOPYRIDINE-N-OXIDE - A CONVENIENT SYNTHESIS OF (L)-VINYLGLYCINE [J].

BARTON, DHR ;

CRICH, D ;

HERVE, Y ;

POTIER, P ;

THIERRY, J .

TETRAHEDRON, 1985, 41 (19) :4347-4357

[9] Organoselenium-based entry into versatile, α-(2-tributylstannyl)vinyl amino acids in scalemic form:: A new route to vinyl stannanes [J].

Berkowitz, DB ;

McFadden, JM ;

Chisowa, E ;

Semerad, CL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (44) :11031-11032

[10]

Berkowitz DB, 2002, ANGEW CHEM INT EDIT, V41, P1603, DOI 10.1002/1521-3773(20020503)41:9<1603::AID-ANIE1603>3.0.CO

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