Enantioselective synthesis of (R)-α-(p-nitroaryl)prolines via oxidative nucleophilic substitution of hydrogen in nitroarenes

Synlett

Volumn , Issue 11, 2008, Pages 1711-1713

  Ma̧kosza, Mieczysław ^a   Sulikowski, Daniel ^a   Maltsev, Oleg ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

Amino acids; Carbanions; Nitroarenes; Oxidative substitution

Indexed keywords

ALDEHYDE DERIVATIVE; AROMATIC NITRO COMPOUND; HYDROGEN; PROLINE DERIVATIVE;

ARTICLE; CHIRALITY; ENANTIOSELECTIVITY; OXIDATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 48249137384     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078483     Document Type: Article

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12. (a) Synthesis of 1 was carried out according a literature procedure (see ref. 10b) with slight modification. Preparation of Compound 1 To a solution of trimethylsilyl ester of N-trimethylsilyl- L-proline (28.8 g, 0.111 mol) in dry n-pentane (23 mL) under argon, pivalaldehyde (12.1 mL, 0.111 mol) was added very slowly. During the addition temperature must be kept below 20 °C cooling in water bath with ice, reaction is exothermic. Overheating the reaction mass above 30 °C cause partial decomposition of the product. After 1 h, the resulting solution was cooled to -70 °C and the crystalline product was filtered and dried; yield 20.3 g, 82%. (a) Annunziata, R.; Ferrari, M.; Papeo, G.; Resmini, M. Synth. Commun. 1997, 27, 23.
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