Optically active pheniramine by enantioselective hydrogenation of unsaturated amines, esters and acids using Ru(II)-complexes with B INAP as catalytic precursors
✍ Scribed by Mauro Marchetti; Elisabetta Alberico; Carlo Bertucci; Carlo Botteghi; Gino Del Ponte
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- English
- Weight
- 589 KB
- Volume
- 125
- Category
- Article
- ISSN
- 1381-1169
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✦ Synopsis
Pheniramine (3a) was prepared throt gh enantioselective hydrogenation of various precursor compounds catalyzed by Ru(II)/BINAP complexes. In the case of N,N-dialkyl-3-phenyl-3-(2-pyridyl)allylamines (1 and 2) only the (Z)-isomer shows a satisfactory reactivity; moreover the chemoselectivity is affected by the hydrogenolysis of the alkylamino group of the substrate. The enantioselectivity did net exceed 50%. 3-Phenyl-3-(2-pyridyl)acrylic acids (9 and 10) and their ethyl esters (5 and 6) gave good chemical yields onl/at reaction temperature >~ 50°C; also in this case poor enantioselectivities (up to 35%) were achieved.