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Volumn 46, Issue 37, 2005, Pages 6219-6221

(R)-2,3-Cyclohexylideneglyceraldehyde, a novel template for stereoselective preparation of functionalized δ-lactones: Synthesis of mosquito oviposition pheromone

Author keywords

(R) 2,3 Cyclohexylideneglyceraldehyde; anti Stereoselectivity; Felkin Anh model; Functionalized lactones; Mosquito oviposition pheromone; Organolithium

Indexed keywords

GLYCERALDEHYDE; LACTONE DERIVATIVE; PHEROMONE;

EID: 23744497665     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.063     Document Type: Article
Times cited : (23)

References (46)
  • 2
    • 0002874969 scopus 로고
    • J.D. Morrison J.W. Scott Academic Press New York
    • J.W. Scott J.D. Morrison J.W. Scott Asymmetric Synthesis Vol. 4 1984 Academic Press New York 1 226
    • (1984) Asymmetric Synthesis , vol.4 , pp. 1-226
    • Scott, J.W.1
  • 3
  • 35
    • 33645197901 scopus 로고    scopus 로고
    • note
    • Method A: n-Bromodecane (0.035 mol) in hexane (50 mL) was added over a period of 2 h to a stirred suspension of finely cut lithium (0.077 mol) in dry hexane (100 mL) at 10-15°C under argon. The mixture was stirred at that temperature for 3 h more when the majority of lithium had dissolved. The suspension was cooled to -40°C. To it a solution of 1 (0.01 mol) in THF (50 mL) was added over a period of 30 min. The mixture was stirred at -40°C for 1 h, at 0°C for 3 h and at room temperature overnight. It was then filtered quickly and the residue containing the unreacted lithium metal was washed with dry THF. [This excess lithium was later decomposed by treatment with cold MeOH.] The combined filtrates were treated with water and extracted with EtOAc. Solvent removal under reduced pressure and column chromatography of the residue (0-20% EtOAc in hexane) afforded 2a and 2b. Method B: n-Bromodecane (0.035 mol) in ether (50 mL) was added over a period of 3 h to a stirred suspension of finely cut lithium (0.077 mol) in dry ether (150 mL) at around -10°C under argon. The mixture was stirred at -10°C for 1 h further to dissolve the most of the lithium. The suspension was cooled to -40°C. To it, a solution of 1 (0.01 mol) in ether (50 mL) was added over a period of 30 min. The mixture was stirred at -40°C for 2 h, at -10°C for 6 h, then filtered. After a normal work up, the products were isolated as in Method A.
  • 40
    • 33645205217 scopus 로고    scopus 로고
    • note
    • 3): δ 0.86 (br t, 3H), 1.04 (s, 9H), 1.2-1.4 (m, 18H), 2.12 (dd, J = 5.4, 2.6 Hz, 1H), 2.45 (dd, J = 5.06, 3.92 Hz, 1H), 2.83-2.98 (m, 1H), 3.38 (dd, J = 11.0, 5.2 Hz, 1H), 7.39 (m, 6H), 7.64 (m, 4H).
  • 41
    • 33645207136 scopus 로고    scopus 로고
    • note
    • 3): δ 0.86 (br t, 3H), 1.04 (s, 9H), 1.2-1.6 (m, 22H overlapped with s at 1.58 for 1H, OH), 1.9-2.05 (m, 2H), 3.4-3.6 (m, 2H), 5.0-5.2 (m, 2H), 5.7-5.9 (m, 1H), 7.36 (m, 6H), 7.65 (m, 4H).
  • 43
    • 33645200810 scopus 로고    scopus 로고
    • note
    • 3): δ 0.86 (t, J = 7.2 Hz, 3H), 1.22 (br m, 16H), 1.4-1.95 (m, 6H), 2.05 (s, 3H), 2.3-2.6 (m, 2H), 4.29-4.32 (m, 1H), 4.9-5.0 (m, 1H).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.