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Transition‐Metal‐Catalyzed Regioselective Asymmetric Mono‐Hydrogenation of Dienes and Polyenes
Author(s) -
Margarita Cristiana,
Rabten Wangchuk,
Andersson Pher G.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201800414
Subject(s) - stereocenter , regioselectivity , catalysis , enantioselective synthesis , double bond , transition metal , chemistry , asymmetric hydrogenation , alkyl , combinatorial chemistry , organic chemistry , organic synthesis
Organic compounds containing multiple C=C bonds are attractive substrates for catalytic asymmetric hydrogenation. The full saturation of prochiral double bonds, controlling the creation of two or more stereocenters in one step, is obviously a remarkable goal. However, another fascinating and useful option is to selectively introduce a new defined stereogenic center while leaving other double bonds untouched. Thus, the retained functionalities can be further exploited in synthesis. Examples of regio‐ and enantioselective mono‐hydrogenations of polyolefins are highlighted in this Concept article, and are divided according to the nature of the reduced double bond and the transition‐metal catalyst used. Alkenes bearing coordinating functional groups are often preferentially hydrogenated by Rh‐ and Ru‐complexes, while the more recently developed Ir‐based catalysts promote the selective saturation on alkyl‐substituted olefins. Relevant applications of this effective methodology in the synthesis of natural products are included to demonstrate its value in organic synthesis.