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Volumn 70, Issue 11, 2005, Pages 1953-1969

Sulfoxide-modified Julia-Lythgoe olefination: Highly stereoselective di-, tri-, and tetrasubstituted double bond formation

Author keywords

Additions; Alkenes; Julia Lythgoe olefination; Olefinations; Reaction mechanisms; Reductive elimination; Samarium; Sulfoxides; Synthetic methods

Indexed keywords


EID: 33644674926     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc20051953     Document Type: Article
Times cited : (8)

References (40)
  • 2
    • 0003417469 scopus 로고
    • (B. M. Trost and I. Fleming, Eds). Pergamon, Oxford
    • b) Kociensky P. J. in: Comprehensive Organic Synthesis (B. M. Trost and I. Fleming, Eds), Vol. 6. Pergamon, Oxford 1991;
    • (1991) Comprehensive Organic Synthesis , vol.6
    • Kociensky, P.J.1
  • 15
    • 33644694133 scopus 로고    scopus 로고
    • note
    • a of the equivalent hydrogen on the carbon bearing the sulfone substituent.
  • 18
    • 33644699246 scopus 로고    scopus 로고
    • note
    • Sulfoxides 1a and 7 were selected because the corresponding sulfones react very poorly (or not at all) under the standard Julia-Lythgoe conditions for electronic (1a) or steric (7) reasons.
  • 19
    • 33644695005 scopus 로고    scopus 로고
    • note
    • The excess of benzoyl chloride was reacted with 3-(dimethylamino)propan- 1-ol (neat) and the amine was removed upon aqueous acid work-up.
  • 20
    • 33644695422 scopus 로고    scopus 로고
    • note
    • All the reactions presented in Table I were carried out on the mixture of adduct 4.
  • 28
    • 33644682258 scopus 로고    scopus 로고
    • note
    • More polar and less polar refer to more and les polar (R,R) or (S,R) diastereoisomers based upon their migration on TLC.
  • 31
    • 33644669716 scopus 로고    scopus 로고
    • National Institute of Advanced Industrial Science and Technology, 23.03
    • SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/ (National Institute of Advanced Industrial Science and Technology, 23.03.2005).
    • (2005)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.