4,4'-Disubstituted BINAPs for highly enantioselective Ru-catalyzed asymmetric hydrogenation of ketones

Organic Letters
Aiguo HuWenbin Lin

Abstract

A family of tunable precatalysts Ru(4,4'-BINAP)(chiral diamine)Cl2 was synthesized and used for highly enantioselective hydrogenation of aromatic ketones. This result differs from previous chiral diphosphines that rely on the bis(xylyl)phosphino groups to control enantioselectivity. An X-ray structural study reveals that the bulky substituents on the 4,4'-positions of BINAP can effectively create a suitable chiral pocket in the transition state and thus provide a new mechanism for the enantiocontrol in such a remarkable asymmetric catalytic process.

References

Oct 26, 2002·The Journal of Organic Chemistry·Jing WuAlbert S C Chan
Dec 12, 2002·Journal of the American Chemical Society·Kamaluddin Abdur-RashidRobert H Morris
Apr 10, 2003·Journal of the American Chemical Society·Jian-Hua XieQi-Lin Zhou
Sep 18, 2003·Journal of the American Chemical Society·Aiguo HuWenbin Lin
Oct 30, 2003·Journal of the American Chemical Society·Christian A SandovalRyoji Noyori
May 6, 2004·Angewandte Chemie·Francis I ValiyaveetilRoderick MacKinnon
Jun 17, 2002·Angewandte Chemie·Ryoji Noyori

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Citations

Jul 6, 2005·Chemical Communications : Chem Comm·Simon BurkWalter Leitner
Jun 15, 2007·Dalton Transactions : an International Journal of Inorganic Chemistry·Christine Sui-SengRobert H Morris
Apr 23, 2013·Chemistry : a European Journal·Agnieszka BartoszewiczBelén Martín-Matute
Jun 25, 2013·Chemistry : a European Journal·Fan JiangChristian Bruneau
Feb 24, 2011·Angewandte Chemie·Torsten IrrgangRhett Kempe
Jun 21, 2013·Chemical Society Reviews·Mariette M PereiraArtur R Abreu
Dec 15, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Hsin-Yi Tiffany ChenC Richard A Catlow
May 12, 2005·Chemical Reviews·Mikaël BerthodMarc Lemaire
Apr 24, 2021·Journal of the American Chemical Society·Hiroaki IwamotoHajime Ito
Feb 12, 2005·The Journal of Organic Chemistry·Helen L Ngo, Wenbin Lin
Nov 10, 2005·The Journal of Organic Chemistry·Yingjian Andy XuMartin Wills

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