A Sequential O‐Nitrosoaldol and Grignard Addition Process: An Enantio‐ and Diastereoselective Entry to Chiral 1,2‐Diols
Authors:
- Masanori KawasakiMKMasanori Kawasaki
- Hisashi YamamotoHYHisashi Yamamoto
- 15 April 2009
- journal article
- Published by Wiley in Angewandte Chemie International Edition
- Vol. 48 (18) , 3333-3336
Abstract
Chiral 1,2-diols have been prepared from alpha-aminoxylated aldehydes or cyclohexanone and Grignard reagents with L-proline or its tetrazole derivative as the catalyst. The presence of the ate complex of CeCl(3)2 LiCl is essential for the high overall yields and good selectivities (see scheme; DMSO = dimethyl sulfoxide, THF = tetrahydrofuran, Tol = tolyl).Keywords
This publication has 49 references indexed in Scilit:
- Concise Total Synthesis and Structure Assignment of TAN‐1085Angewandte Chemie International Edition, 2004
- Concise Total Synthesis and Structure Assignment of TAN-1085Angewandte Chemie, 2004
- Pinacol Coupling2000
- Design, Synthesis, and Application of a C2 Symmetric Chiral Ligand for Enantioselective Conjugate Addition of Organolithium to α,β-Unsaturated AldimineThe Journal of Organic Chemistry, 1998
- Catalytic Asymmetric Oxidation of Aryl Sulfides with a Ti/H2O/(R,R)-Diphenylethane-1,2-diol Complex: a Versatile and Highly Enantioselective Oxidation ProtocolThe Journal of Organic Chemistry, 1998
- Novel cationic titanium(IV) Lewis acids and their use in asymmetric aldol reactionsTetrahedron, 1998
- New Developments in the Chemistry of Low‐Valent TitaniumAngewandte Chemie International Edition, 1996
- Neue Entwicklungen in der Chemie von niedervalentem TitanAngewandte Chemie, 1996
- C2-symmetric chiral zinc alkoxides as catalysts for the enantioselective addition of diethylzinc to aryl aldehydesTetrahedron: Asymmetry, 1996
- On the addition of nitroso-compounds to conjugated systemsCollection of Czechoslovak Chemical Communications, 1949