Chiral Ligands Derived from Monoterpenes: Application in the Synthesis of Optically Pure Secondary Alcohols via Asymmetric Catalysis

• Published in: Chemistry : a European journal Vol. 21; no. 4; pp. 1398 - 1413
• Main Authors: El Alami, Mohammed Samir Ibn, El Amrani, Mohamed Amin, Agbossou-Niedercorn, Francine, Suisse, Isabelle, Mortreux, André
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 19.01.2015; WILEY‐VCH Verlag; Wiley Subscription Services, Inc; Wiley-VCH Verlag
• Series: Chemistry - A European Journal
• Subjects: Alcohols; Alcohols - chemical synthesis; Alcohols - chemistry; Aldehydes; asymmetric catalysis; Bonding; Catalysis; Catalysts; Chemical industry; Chemical Sciences; Chemistry; Chemistry Techniques, Synthetic - methods; chiral ligands; Coordination chemistry; Hydrogen; Hydrosilylation; Ligands; Monoterpenes - chemical synthesis; Monoterpenes - chemistry; natural product synthesis; terpenes; alcohols; asymmetric catalysis; chiral ligands; natural product synthesis; terpenes
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201404303

The preparation of optically pure secondary alcohols in the presence of catalysts based on chiral ligands derived from monoterpenes, such as pinenes, limonenes and carenes, is reviewed. A wide variety of these ligands has been synthesized and used in several catalytic reactions, including hydrogen transfer, CC bond formation via addition of organozinc compounds to aldehydes, hydrosilylation, and oxazaborolidine reduction, leading to high activities and enantioselectivities. The preparation of chiral secondary alcohols in the presence of catalysts based on optically pure ligands derived from monoterpenes, such as pinenes, limonenes and carenes, is reviewed. A large variety of these ligands has been synthesized and used in catalytic reactions, including hydrogen transfer, CC bond formation via addition of organozinc reagents to aldehydes, hydrosilylation, and oxazaborolidine reductions.