Asymmetric conjugate reduction of α,β-unsaturated esters with chiral rhodium(bisoxazolinylphenyl) catalysts

Synlett

Volumn , Issue 14, 2004, Pages 2493-2496

  Tsuchiya, Yasunori ^a   Kanazawa, Yoshinori ^a   Shiomi, Takushi ^a   Kobayashi, Kazuki ^a   Nishiyama, Hisao ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Asymmetric catalysis; Conjugate reduction; Hydrosilylation; Rhodium; Unsaturated ester

Indexed keywords

ESTER; RHODIUM (BISOXAZOLINYLPHENYL) DERIVATIVE; RHODIUM DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; ENANTIOSELECTIVITY; REDUCTION;

EID: 9644266678     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-834791     Document Type: Article

References (40)

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35. -1. The structure of 1 was also determined by elemental analysis and X-ray analysis of a single crystal, which will be disclosed elsewhere,
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37. Typical Reaction (Run 1 of Table 1). To a mixture of ethyl (E)-3-phenyl-2-butenoate (4, 190 mg, 1.00 mmol) and the catalyst 1 (5.4 mg, 0.01 mmol) in 1 mL of toluene was slowly added diethoxymethylsilane (201 mg, 1.50 mmol) at 60 °C. The mixture was stirred for 1 h and then treated with 1 N HCl (1 mL). After extraction and concentration, the residue was purified by silica gel chromatography (EtOAc-hexane) to give the reduction product (R)-(-)-5 of 184 mg (96%) as colorless oil. For characterization, see ref. 3a,4c. The unsaturated esters were synthesized by Horner-Emmons reaction; see ref. 3a.
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40. (c) The ee of (3S)-(-)-13 was determined by GC with Alltech Chiraldex G-TA(105 °C, 80 kPa).