Efficient, Rhodium‐Catalyzed Hydrogenation of α‐Dehydroamino Acid Esters with Chiral Monodentate Aminophosphanes Bearing Two Binaphthyl Groups | Zendy

Eberhardt Luc | Zendy; Armspach Dominique | Zendy; Matt Dominique | Zendy; Toupet Loic | Zendy; Oswald Benoît | Zendy

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Efficient, Rhodium‐Catalyzed Hydrogenation of α‐Dehydroamino Acid Esters with Chiral Monodentate Aminophosphanes Bearing Two Binaphthyl Groups

Author(s) -

Eberhardt Luc,

Armspach Dominique,

Matt Dominique,

Toupet Loic,

Oswald Benoît

Publication year - 2007

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200700533

Subject(s) - chemistry , rhodium , denticity , catalysis , asymmetric hydrogenation , medicinal chemistry , azepine , stereochemistry , organic chemistry , enantioselective synthesis , crystal structure

All four stereoisomers of 4‐{4,5‐dihydro‐3 H ‐dinaphtho[2,1‐ c :1′,2′‐ e ]azepin‐4‐yl}dinaphtho[2,1‐ d :1′,2′‐ f ][1,3,2]dioxaphosphepine have been prepared from ( R or S )‐1,1′‐binaphthyl‐2,2′‐diyl chlorophosphite and the appropriate dinaphtho‐azepine. When reacted with [Rh(1,5‐cyclooctadiene) 2 ]BF 4 , highly active catalysts for the hydrogenation of α‐dehydroamino acid esters were obtained. The highest enantioselectivities (up to 99 % ee ) were achieved with the phosphoramidites having two chiral binaphthyl groups with opposite configurations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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