Asymmetric alkylation of aromatic aldehydes with diethylzinc catalyzed by a fluorous BINOL-Ti complex in an organic and fluorous biphase system

Tetrahedron Letters

Volumn 41, Issue 1, 2000, Pages 57-60

  Nakamura, Yutaka ^a   Takeuchi, Seiji ^a   Ohgo, Yoshiaki ^a   Curran, Dennis P ^b  

^a NIIGATA UNIVERSITY OF PHARMACY AND APPLIED LIFE SCIENCES   (Japan)

^b UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

Alkylation; Asymmetric; Catalysis; Fluorine; Fluorine compounds

Indexed keywords

ALDEHYDE; FLUORINE; FLUORINE DERIVATIVE; METAL COMPLEX; TITANIUM; ZINC DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; SYNTHESIS;

EID: 0033992283     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01999-1     Document Type: Article

References (20)

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15. R=8.9 min.
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18. 5) were used as the chiral ligand and the solvent. The work-up procedure was similar to that described in the text. The enantioselectivities and the yields for several aromatic aldehydes were as follows: benzaldehyde (84% ee, 92%); 3-methoxybenzaldehyde (85% ee, 95%), 4-methoxybenzaldehyde (80% ee, 97%), 1-naphthylaldehyde (91% ee, 98%), 2-naphthylaldedehyde (78% ee, 93%). (R)-FBINOL was recovered quantitatively and was reusable.
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