A new chiral 2-sulfonylamino-2′-phosphino-1,1′-binaphthyl ligand for highly enantioselective copper-catalyzed conjugate addition of diethylzinc to benzylideneacetones

Tetrahedron Letters

Volumn 45, Issue 29, 2004, Pages 5717-5722

  Morimoto, Toshiaki ^a   Mochizuki, Nobuhiro ^a   Suzuki, Masato ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

Chiral binaphthyl ligand; Conjugate addition; Copper catalyst; Enantioselectivity; Enones

Indexed keywords

2 SULFONYLAMINO 2' PHOSPHINO 1,1' BINAPHTHYL; BENZYLIDENE DERIVATIVE; BENZYLIDENEACETONE; COPPER; DIETHYLZINC; NAPHTHYL GROUP; UNCLASSIFIED DRUG;

ADDITION REACTION; AMIDATION; ARTICLE; CHIRALITY; CONJUGATION; ENANTIOSELECTIVITY; HYDROLYSIS; ISOMERISM; QUANTUM YIELD; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 3042618784     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.101     Document Type: Article

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59. 4, filtered, and concentrated in vacuo. The crude product was purified by silica gel column chromatography (hexane/AcOEt=3/1) to give the corresponding 1, 4-addition product, 4-phenylhexan-2-one 13. The yields and the ee values of the addition products were determined by GC analysis (before or after purification) with a chiral capillary column, Superco γ-DEX 225 or HPLC analysis with a chiral column, Daicel Chiralcel OJ
60. The highest ee value was obtained in toluene, though it was not clearly explained that the yield of the product in toluene was lower than those obtained in other solvents or by using smaller molar ratios of the ligand to copper triflate. The lower yield may be rationalized by the explanation that a considerable part of copper complexes (higher ratios of ligand to copper: 2/1 or/and more) formed are less active (aggregated, less soluble in toluene; less active as a catalyst for the conjugate addition but active for by-reactions)
61. For further evaluation of the ligand, the reaction of a representative cyclic enone, 2-cyclohexen-1-one with diethylzinc was also carried out under similar conditions, affording (R)-3-ethylcyclohexan-1-one in lower selectivity (52% ee)