SCOPUS 정보 검색 플랫폼

Volumn , Issue 12, 2007, Pages 1925-1929

Synthesis of α-amino acids via a carbolithiation reaction on acyclic ene-carbamates and an internal N→C alkyloxycarbonyl migration

Author keywords

Alkyloxycarbonyl migration; Carbolithiation; Ene carbamate; Non natural amino acids; Vinyl phosphate

Indexed keywords

ALPHA AMINO ACID; CARBAMIC ACID DERIVATIVE; CARBONYL DERIVATIVE; LITHIUM CARBONATE; OXYCARBONYL; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CROSS COUPLING REACTION; SUZUKI REACTION; SYNTHESIS;

EID: 34547615213 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-984874 Document Type: Article

Times cited : (23)

References (25)

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21
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- Representative Procedure for the Preparation of 7a-1 A solution of acyclic ene-carbamate 4a (0.100 g, 0.34 mmol) in THF (10 mL) was cooled to -78°C under argon. Subsequently, MeLi (0.450 mL, 1.4 M in hexane, 0.71 mmol) was added dropwise. After stirring for 30 min at -78°C, the reaction mixture was warmed up to 0°C. After 1 h at 0°C, the reaction was quenched by slow addition of H2O. The aqueous phase was then extracted with EtOAc and the organic phase was washed with brine. The organic phase was dried over anhyd MgSO4 and concentrated. Flash chromatography (PE-EtOAc, 98:2) afforded 7a (75, as a white solid; mp 109-110°C. IR (KBr, 3419, 2980, 1720, 1599, 1504, 1158 cm-1. 1H NMR (250 MHz, CDCl3, δ, 7.56 (d, J, 7.6 Hz, 2 H, 7.20-7.32 (m, 3 H, 6.95 (t, J, 7.8 Hz, 2 H, 6.57 (t, J, 7.6 Hz, 1 H, 6.35 (d, J, 7.8 Hz, 2 H, 5.35 (br s, 1 H, 2.51 m, 2 H
- +.

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24
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- N→C Acyl migration: Rouden, J.; Ragot, A.; Gouault, S.; Cahard, D.; Plaquevent, J.-C.; Lasne, M.-C. Tetrahedron: Asymmetry 2002, 13, 1299.

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