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Room Temperature Highly Enantioselective Nickel‐Catalyzed Hydrovinylation
Author(s) -
Lassauque Nicolas,
Franciò Giancarlo,
Leitner Walter
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900559
Subject(s) - chemistry , phosphoramidite , catalysis , enantioselective synthesis , nickel , amine gas treating , combinatorial chemistry , medicinal chemistry , organic chemistry , dna , biochemistry , oligonucleotide
At room temperature, nickel catalysts based on the new phosphoramidite (11b R )‐ N ‐[( S )‐1‐(naphthalen‐1‐yl)ethyl]‐ N ‐[( S )‐1‐(naphthalen‐2‐yl)ethyl]dinaphtho[2,1‐ d :1′,2′‐ f ][1,3,2]dioxaphosphepin‐4‐amine provide excellent selectivities for 3‐arylbut‐1‐enes (93–99%) with high enantioselectivities (90–95% ee ) and TOFs (up to 8300 h −1 ) in the hydrovinylation of electron‐rich and electron‐poor vinylarenes. Within a few minutes, useful chiral building blocks and intermediates can be synthesized using this practical catalytic system.