Catalyzed asymmetric dialkylzinc addition to benzaldehyde in the presence of new chiral ligands - δ-(1-Phenethyl)aminoalcohols

Chirality

Volumn 13, Issue 8, 2001, Pages 507-509

  Demyanovich, V M ^a   Shishkina, I N ^a   Zefirov, N S ^a  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

1 Phenethylamine; Absolute configuration; Aminoalcohol; Enantiose lectivity; Optical rotation; Optically active alcohol

Indexed keywords

AMINOALCOHOL; BENZALDEHYDE; PHENETHYL ALCOHOL; ZINC DERIVATIVE;

CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CHIRALITY; CONFERENCE PAPER; ENANTIOMER; PRIORITY JOURNAL; SYNTHESIS;

EID: 0034899334     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.1068     Document Type: Conference Paper

References (10)

1. Corey EJ, Guzman-Perez A. The catalytic enantioselective construction of molecules with quaternary carbon Stereocenters. Angew Chem Int Ed Engl 1998;37:388-401.
2. Soai K, Niwa S. Enantioselective addition of organozinc reagents to aldehydes. Chem Rev 1992;92:833-856.
3. Knollmüller M, Ferencic M, Gaertner P. Enantioselective addition of organometallics to aldehydes using camphor derived chiral 1,4-aminoalcohols as ligands. Tetrahedron: Asymmetry 1999;10:3969-3976.
4. Demyanovich VM, Shishkina IN, Vedernikov AI. Lithiation of (S)-(-)-N,N-Dimethyl-1-phenethylamine. Zh Org Chim 1991;27:2628-2629.
5. Demyanovich VM, Shishkina IN, Vedernikov AI, Tafeenko VA, Aslanov LA, Zeflrov NS. New chiral ligands. Synthesis and absolute configuration of diasteremeric [o-(α-dimethylaminoethyl)phenyl]trifuoromethylphenyl-carbinols. Dokl Akad Nauk 1993;330:324-326.
6. Shishkina IN. Synthesis of new chiral ligands on the base of 1-phenethylamine. PhD Thesis. Moscow State University; 1998.
7. Panov VN, Potekhin KA, Struchkov UT, Shishkina IN, Demyanovich VM, Zefirov NS. The molecular and crystal structure of (S,S)-[o-(α-dimethylaminoethyl)phenyl]phenylarylcarbinols. Crystallogr Rep 2000;45:604-610.
8. Demyanovich VM, Shishkina IN, Potekhin KA, Zefirov NS. Synthesis and absolute configuration of (S,S)-[o-(1-dimethylaminoethyl)phenyl]phenyl-3,4-dimethoxyphenylcarbinol. Dokl Akad Nauk 2001 (in press).
9. Demyanovich VM, Shishkina IN, Zefirov NS. Absolute configuration and circular dichroism of triarylcarbinols. Proc 5th Int Conf Circular Dichroism, Colorado (USA). Aug., 1993; p 232.
10. Watanabe M, Araki S, Butsugan Y. Chiral auxiliaries for asymmetric synthesis: enantioselective addition of dialkylzinc to aldehydes catalyzed by chiral 1,2-disubstituted ferrocenyl aminoalcohols. J Org Chem 1991;56:2218-2224