Enantiomerically pure α-amino acid synthesis via hydroboration -: Suzuki cross-coupling

被引：83

作者：

Collier, PN

Campbell, AD

Patel, I

Raynham, TM

Taylor, RJK ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

[2] AstraZeneca, Avlon Works, Bristol BS10 7ZE, Avon, England

[3] Roche Discovery Welwyn, Welwyn Garden City AL7 3AY, Herts, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 06期

关键词：

D O I：

10.1021/jo010865a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Garner aldehyde-derived methylene alkene 5 and the corresponding benzyloxycarbonyl compound 25 undergo hydroboration with 9-BBN-H followed by palladium-catalyzed Suzuki coupling reactions with aryl and vinyl halides. After one-pot hydrolysis-oxidation, a range of known and novel nonproteinogenic amino acids were isolated as their N-protected derivatives. These novel organoborane homoalanine anion equivalents are generated and transformed under mild conditions and with wide functional group tolerance: electron-rich and -poor aromatic iodides and bromides (and a vinyl bromide) all undergo efficient. Suzuki coupling. The extension of this methodology to prepare meso-DAP, R,R-DAP, and R,R-DAS is also described.

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页码：1802 / 1815

页数：14

相关论文

共 70 条

[1] Synthesis of diaminosuberic acid derivatives via ring-closing alkyne metathesis [J].

Aguilera, B ;

Wolf, LB ;

Nieczypor, P ;

Rutjes, FPJT ;

Overkleeft, HS ;

van Hest, JCM ;

Schoemaker, HE ;

Wang, B ;

Mol, JC ;

Fürstner, A ;

Overhand, M ;

van der Marel, GA ;

van Boom, JH .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (10) :3584-3589

[2]

Arakawa Y, 1998, CHEM PHARM BULL, V46, P674

[3] SYNTHESIS OF OPTICALLY PURE ALPHA-AMINO-ACIDS VIA SALTS OF ALPHA-AMINO-BETA-PROPIOLACTONE [J].

ARNOLD, LD ;

MAY, RG ;

VEDERAS, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) :2237-2241

[4] NON-PROTEINOGENIC AMINO-ACID SYNTHESIS - SYNTHESIS OF BETA, GAMMA-UNSATURATED ALPHA-AMINO-ACIDS FROM ASPARTIC-ACID [J].

BALDWIN, JE ;

MOLONEY, MG ;

NORTH, M .

TETRAHEDRON, 1989, 45 (19) :6319-6330

[5]

BARRETT GC, 1985, CHEM BIOCH AMINO ACI

[6] SYNTHESIS OF NOVEL ALPHA-AMINO-ACIDS AND DERIVATIVES USING RADICAL CHEMISTRY - SYNTHESIS OF L-ALPHA-AMINO-ADIPIC AND D-ALPHA-AMINO-ADIPIC ACIDS, L-ALPHA-AMINOPIMELIC ACID AND APPROPRIATE UNSATURATED DERIVATIVES [J].

BARTON, DHR ;

HERVE, Y ;

POTIER, P ;

THIERRY, J .

TETRAHEDRON, 1987, 43 (19) :4297-4308

[7] PREPARATION AND USE OF C2-SYMMETRICAL BIS(PHOSPHOLANES) - PRODUCTION OF ALPHA-AMINO-ACID DERIVATIVES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION REACTIONS [J].

BURK, MJ ;

FEASTER, JE ;

NUGENT, WA ;

HARLOW, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10125-10138

[8] Stereoselective synthesis of diaminosuberic acid via a chiral alkynyl oxazolidine [J].

Callahan, JF ;

Khatana, SS ;

Bhatnagar, PK .

SYNTHETIC COMMUNICATIONS, 2000, 30 (07) :1213-1219

[9] exo-glycal approaches to C-linked glycosyl amino acid synthesis [J].

Campbell, AD ;

Paterson, DE ;

Raynham, TM ;

Taylor, RJK .

CHEMICAL COMMUNICATIONS, 1999, (16) :1599-1600

[10]

Campbell AD, 1998, SYNTHESIS-STUTTGART, P1707

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