Enantio- and diastereoselective construction of vicinal quaternary and tertiary carbon centers by catalytic Michael reaction of α-substituted β-keto esters to cyclic enones

Tetrahedron Letters

Volumn 46, Issue 32, 2005, Pages 5377-5381

  Majima, Keisuke ^a   Tosaki, Shin Ya ^a   Ohshima, Takashi ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Substituted keto ester; Catalytic enantio and diastereoselective Michael reaction; La complex

Indexed keywords

CARBON; ESTER DERIVATIVE; LANTHANIDE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; DIASTEREOISOMER; ENANTIOMER; ENANTIOSELECTIVITY; ISOMER; MICHAEL ADDITION; QUANTITATIVE ANALYSIS; QUANTUM YIELD; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 21844446898     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.05.139     Document Type: Article

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37. For the screening of reaction conditions, we used 3a and 4a as substrates because enantiomeric excess of the product 5aa was easily determined by chiral GC analysis after acetalization of the cyclic ketone.
38. In the catalytic enantioselective Michael reaction of α-non-substituted β-keto esters to cyclic enones, we proposed that at least one β-keto ester should be included in the active catalyst complex. See Ref. 10.
39. For the syntheses of ligands 6a-g and 7, see Supplementary data.
40. 2, hexane/ethyl acetate, 9/1) to give 5ab (43.3 mg, 0.18 mmol, 89%, 86/14 dr, 82% ee for both diastereomers).
41. In all entries, the absolute configurations of β-position of the acceptors were determined to be R by chemical correlation. The relative configurations were determined by NOE (5ab and bc ), X-ray (5bh ), and chemical correlation (5aa, ac, ad, af, bb, bd, be, bf, bg, cc, cd, and cf ). For details, see Supplementary data. Crystallographic data for 10bh have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 272617.