Biaryl phosphite-oxazolines from hydroxyl aminoacid derivatives: highly efficient modular ligands for Ir-catalyzed hydrogenation of alkenes.
نویسندگان
چکیده
High enantioselectivities and activities are achieved in the Ir-catalyzed hydrogenation of several unfunctionalized olefins using modular biaryl phosphite-oxazoline ligands from hydroxyl aminoacid derivatives; the presence of a biaryl phosphite group is crucial to this success.
منابع مشابه
Synthesis of a new class of conformationally rigid phosphino-oxazolines: highly enantioselective ligands for Ir-catalyzed asymmetric hydrogenation.
[reaction: see text] A new class of conformationally rigid phosphino-oxazoline ligands were synthesized from readily available enantiopure phenyl glycinol. Ir complexes with these ligands are air-stable and highly enantioselective catalysts for asymmetric hydrogenation of aryl alkenes and alpha,beta-unsaturated esters in up to 99% ee.
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Hydrogenation of a series of cyclic beta-(acylamino)acrylates with tetrasubstituted olefins has been accomplished successfully with the use of Ru catalysts with chiral biaryl ligands such as C3-TunaPhos, and up to over 99% ee's have been achieved. This methodology provides an efficient catalytic method for the synthesis of both cis and trans chiral cyclic beta-amino acid derivatives.
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The hydrogenation of 2-methylquinoline with Ir catalysts based on chiral phosphine-phosphites has been investigated. It has been observed that the reaction is very sensitive to the nature of the ligand. Optimization of the catalyst, allowed by the highly modular structure of these phosphine-phosphites, has improved the enantioselectivity of the reaction up to 73% ee. The influence of additives ...
متن کاملA new class of readily available and conformationally rigid phosphino-oxazoline ligands for asymmetric catalysis
A new class of conformationally rigid phosphino-oxazoline ligands 3 were synthesized via an efficient ortho-substitution of phenyl glycinol as the key step. Divergent synthetic routes for easy ligand modulation, as well as a procedure suitable for scale-up synthesis, were established. The catalytic potential of ligands 3 has been demonstrated in the highly enantioselective Ir-catalyzed hydrogen...
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ورودعنوان ژورنال:
- Chemical communications
دوره 33 شماره
صفحات -
تاریخ انتشار 2008