☆ 4.7 Article

Rhodium-Catalyzed Asymmetric Hydroformylation of 1,1-Disubstituted Allylphthalimides: A Catalytic Route to 3-Amino Acids

ADVANCED SYNTHESIS & CATALYSIS (2013)

Journal

ADVANCED SYNTHESIS & CATALYSIS

Volume 355, Issue 4, Pages 679-684

Publisher

WILEY-V C H VERLAG GMBH

DOI: 10.1002/adsc.201200960

Keywords

allylphthalimides; 3-amino acids; 3-amino alcohols; 3-amino aldehydes; asymmetric catalysis; enantioselectivity; hydroformylation; rhodium

Categories

Chemistry, Applied Chemistry, Organic

Funding

National Science Foundation [NSF CHE 0956784]
China Scholarship Council
Direct For Mathematical & Physical Scien
Division Of Chemistry [0956784] Funding Source: National Science Foundation

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Abstract

The high enantioselective rhodium-catalyzed hydroformylation of 1,1-disubstituted allylphthalimides has been developed. By employing chiral ligand 1,2-bis[(2S,5S)-2,5-diphenylphospholano]ethane [(S,S)-Ph-BPE], a series of 3-aminoaldehydes can be prepared with up to 95% enantioselectivity. This asymmetric procedure provides an efficient alternative route to prepare chiral 3-amino acids and alcohols.

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