A practical and controllable enantioselective synthesis of 2-phenyl-1-cyclopropanecarboxylates via a camphor-derived sulfonium ylide

Synlett

Volumn , Issue 10, 2005, Pages 1621-1623

  Huang, Kun ^a   Huang, Zhi Zhen ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

Cyclopropanecarboxylate; Diastereoselectivity; Enantioselective synthesis; Practical method; Sulfonium ylide

Indexed keywords

2 PHENYL 1 CYCLOPROPANECARBOXYLATE; CAMPHOR; CARBOXYLIC ACID DERIVATIVE; SULFONIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CYCLOPROPANATION; DIASTEREOISOMER; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 21544442891     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-869852     Document Type: Article

References (16)

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9. 1H NMR: δ = 7.60 - 7.27 (m, 5 H), 6.21 (d, J = 7.4 Hz, 1 H), 5.71 (d, J = 12.0 Hz, 1 H), 5.51 (d, J = 12.0 Hz, 1 H), 4.54 (d, J = 7.4 Hz, 1 H), 4.11 (t, J = 7.4 Hz, 1 H), 2.86 (s, 3 H), 1.97 (d, J = 4.5 Hz, 1 H), 1.84-1.80 (m, 1 H), 1.66 (s, 1 H), 1.46-1.29 (m, 2 H), 1.15 (s, 3 H), 0.95 (s, 3 H), 0.81 (s, 3 H). MS (ESI): m/z = 291.1 (M-Br).
10. General procedure for the controllable enantioselective synthesis of 2-phenyl-1-cyclopropanecarboxylates 7c-f via camphor-derived sulfonium ylide 9: To a stirred suspension of sulfonium salt 8 (445 mg, 1.2 mmol) and α,β-unsaturated ester (1.0 mmol) in THF (6 mL) was added t-BuOK (336 mg, 3.0 mmol) or NaH (72 mg, 3.0 mmol) in one portion at the desired temperature (Table 1). After stirring for the time indicated (Table 1), the reaction mixture was passed through a short silica gel column, which was eluted with ethyl acetate. After concentration of the eluent, the residue was purified by flash column chromatography or preparative TLC, giving 2-phenyl-1- cyclopropanecarboxylate 7c-f.
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