Catalytic asymmetric cyano-phosphorylation of aldehydes promoted by heterobimetallic YLi3tris(binaphthoxide) (YLB) complex

Synlett

Volumn , Issue 13, 2004, Pages 2434-2436

  Abiko, Yumi ^a   Yamagiwa, Noriyuki ^a   Sugita, Mari ^a   Tian, Jun ^a   Matsunaga, Shigeki ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Asymmetric catalysis; Cyanohydrins; Lewis acid; Phosphorylation; Yttrium

Indexed keywords

ALDEHYDE DERIVATIVE; CYANOHYDRIN; LITHIUM DERIVATIVE; METAL DERIVATIVE; NAPHTHALENE DERIVATIVE; NITRILE; OXIDE; PHOSPHINE DERIVATIVE; YTTRIUM;

ADDITION REACTION; ARTICLE; ASYMMETRIC CATALYSIS; ENANTIOSELECTIVITY; PHOSPHORYLATION; QUANTUM YIELD; REACTION ANALYSIS;

EID: 8644281973     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-832821     Document Type: Article

References (25)

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23. The phosphine oxides 3 were synthesized form corresponding phosphines: Kim, R. D.; Stevens, C. H. Polyhedron 1994, 13, 727.
24. 3; 92% ee, R); HPLC (DAICEL CHIRALPAK®) AD-H, hexane-2-PrOH = 9:1, flow rate = 1.0 mL/min, retention time 14.5 min (S)/17.1 min (R). The absolute configuration of 6a was determined comparing retention time in HPLC analysis with that of the authentic product synthesized from commercially available (R)-mandelonitrile (Aldrich Co. Ltd.) with 4.
25. Detailed mechanistic studies of asymmetric cyanation reaction using YLB(1) and the cyanide source 2 and 4 will be reported elsewhere in due course.