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Catalytic enantioselective organozinc addition toward optically active tertiary alcohol synthesis.
Chem Rec. 2008; 8(3):143-55.CR

Abstract

A highly enantioselective organozinc (R2Zn) addition to a series of aldehydes and ketones was developed based on conjugate Lewis acid-Lewis base catalysis. Optically active secondary and tertiary alcohols were obtained in high yields with high enantioselectivities without Ti(IV) compounds. Bifunctional chiral 3,3'-diphosphoryl-BINOL ligands were designed and prepared through a phospho-Fries rearrangement as a key step. On the other hand, bifunctional chiral phosphoramide ligands were designed and prepared from L-valine. Mechanistic studies were performed by X-ray analyses of Zn(II) cluster and chiral ligands, a 31P NMR experiment on Zn(II) complexes, and stoichiometric reactions with some chiral or achiral Zn(II) complexes to propose a transition state assembly that includes monomeric active intermediates.

Authors+Show Affiliations

Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya, 464-8603, Japan.No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

18563831

Citation

Hatano, Manabu, and Kazuaki Ishihara. "Catalytic Enantioselective Organozinc Addition Toward Optically Active Tertiary Alcohol Synthesis." Chemical Record (New York, N.Y.), vol. 8, no. 3, 2008, pp. 143-55.
Hatano M, Ishihara K. Catalytic enantioselective organozinc addition toward optically active tertiary alcohol synthesis. Chem Rec. 2008;8(3):143-55.
Hatano, M., & Ishihara, K. (2008). Catalytic enantioselective organozinc addition toward optically active tertiary alcohol synthesis. Chemical Record (New York, N.Y.), 8(3), 143-55. https://doi.org/10.1002/tcr.20146
Hatano M, Ishihara K. Catalytic Enantioselective Organozinc Addition Toward Optically Active Tertiary Alcohol Synthesis. Chem Rec. 2008;8(3):143-55. PubMed PMID: 18563831.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic enantioselective organozinc addition toward optically active tertiary alcohol synthesis. AU - Hatano,Manabu, AU - Ishihara,Kazuaki, PY - 2008/6/20/pubmed PY - 2008/8/1/medline PY - 2008/6/20/entrez SP - 143 EP - 55 JF - Chemical record (New York, N.Y.) JO - Chem Rec VL - 8 IS - 3 N2 - A highly enantioselective organozinc (R2Zn) addition to a series of aldehydes and ketones was developed based on conjugate Lewis acid-Lewis base catalysis. Optically active secondary and tertiary alcohols were obtained in high yields with high enantioselectivities without Ti(IV) compounds. Bifunctional chiral 3,3'-diphosphoryl-BINOL ligands were designed and prepared through a phospho-Fries rearrangement as a key step. On the other hand, bifunctional chiral phosphoramide ligands were designed and prepared from L-valine. Mechanistic studies were performed by X-ray analyses of Zn(II) cluster and chiral ligands, a 31P NMR experiment on Zn(II) complexes, and stoichiometric reactions with some chiral or achiral Zn(II) complexes to propose a transition state assembly that includes monomeric active intermediates. SN - 1528-0691 UR - https://www.unboundmedicine.com/medline/citation/18563831/Catalytic_enantioselective_organozinc_addition_toward_optically_active_tertiary_alcohol_synthesis_ L2 - https://doi.org/10.1002/tcr.20146 DB - PRIME DP - Unbound Medicine ER -