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)

被引：39

作者：

Avenoza, A ^{[1
]}

Cativiela, C

Corzana, F

Peregrina, JM

Zurbano, MM

机构：

[1] Univ La Rioja, Dept Quim Quim Organ, Logrono 26001, Spain

[2] Univ Zaragoza, CSIC, Inst Ciencia Mat Aragon, Dept Quim Organ, E-50009 Zaragoza, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 22期

关键词：

D O I：

10.1021/jo990957o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This report describes an efficient and convenient large-scale synthesis procedure for (S)- and (R)-N-Boc-alpha-methylserinal acetonides (3 and 4) starting from (R)-2-methylglycidol 5. The application of both of these compounds as valuable chiral building blocks in the asymmetric synthesis of alpha-methylamino acids is also demonstrated by the synthesis of(S)- and (R)-isovalines (Iva) (6 and 7).

引用

页码：8220 / 8225

页数：6

共 58 条

[1] ENANTIOSPECIFIC AND DIASTEREOSELECTIVE SYNTHESIS OF 4,4-DISUBSTITUTED-3-AMINO-2-AZETIDINONES, STARTING FROM D-SERINE [J].

AGENO, G ;

BANFI, L ;

CASCIO, G ;

GUANTI, G ;

MANGHISI, E ;

RIVA, R ;

ROCCA, V .

TETRAHEDRON, 1995, 51 (29) :8121-8134

[2] Synthesis of (S)-N-tert-butoxycarbonyl-N,O-isopropylidene-α-methylserinal:: A potential building block for the asymmetric synthesis of non-natural amino acids [J].

Alías, M ;

Cativiela, C ;

Díaz-de-Villegas, MD ;

Gálvez, JA ;

Lapeña, Y .

TETRAHEDRON, 1998, 54 (49) :14963-14974

[3]

Avenoza A, 1997, SYNTHESIS-STUTTGART, P1146

[4] Synthesis of meso-2,4-diaminoglutaric acid. [J].

Avenoza, A ;

Cativiela, C ;

Peregrina, JM ;

Zurbano, MM .

TETRAHEDRON-ASYMMETRY, 1996, 7 (06) :1555-1558

[5] Asymmetric synthesis of meso- and (2R,4R)-2,4-diaminoglutaric acids [J].

Avenoza, A ;

Cativiela, C ;

Peregrina, JM ;

Zurbano, MM .

TETRAHEDRON-ASYMMETRY, 1997, 8 (06) :863-871

[6] SYNTHESIS OF CHIRAL VINYLGLYCINES [J].

BEAULIEU, PL ;

DUCEPPE, JS ;

JOHNSON, C .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4196-4204

[7] Synthesis and biological properties of new constrained CCK-B antagonists: Discrimination of two affinity states of the CCK-B receptor on transfected CHO cells [J].

Bellier, B ;

McCortTranchepain, I ;

Ducos, B ;

Danascimento, S ;

Meudal, H ;

Noble, F ;

Garbay, C ;

Roques, BP .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (24) :3947-3956

[8] GENERATION AND CYCLOADDITIONS OF 4,5-DIHYDROOXAZOLE-4-CARBONITRILE AND OXAZOLIDINE-4-CARBONITRILE N-OXIDES [J].

BLAKE, AJ ;

BOYD, EC ;

GOULD, RO ;

PATON, RM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (19) :2841-2847

[9] STEREOSELECTIVE CYCLOADDITION OF NITRILE OXIDES TO 4-VINYL-OXAZOLINES AND 4-VINYL-OXAZOLIDINES [J].

BOYD, EC ;

PATON, RM .

TETRAHEDRON LETTERS, 1993, 34 (19) :3169-3172

[10] Stereoselective synthesis of quaternary α-amino acids.: Part 1:: Acyclic compounds [J].

Cativiela, C ;

Diaz-de-Villegas, MD .

TETRAHEDRON-ASYMMETRY, 1998, 9 (20) :3517-3599

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