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Volumn , Issue 10, 2006, Pages 1583-1585

A novel synthesis of bicyclo[3.3.0]octane ring system via a desymmetric C-H insertion reaction

Author keywords

Bicyclo 3.3.0 octane ring; C H insertion; Chiral auxiliary; Piperidinyl mandelamide; Rh2(S DOSP)4

Indexed keywords

BICYCLO[3.3.0]OCTANE DERIVATIVE; CARBENOID; CYCLOPENTANONE DERIVATIVE; DIHYDROBENZOFURAN DERIVATIVE; METHENAMINE MANDELATE; PIPERIDINE DERIVATIVE; PIPERIDINYL MANDELAMIDE; RHODIUM DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33745683793     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-941603     Document Type: Article
Times cited : (13)

References (25)
  • 10
    • 0029928212 scopus 로고    scopus 로고
    • Chiral alcohols 11a and 11b were synthesized from the corresponding lactate and mandelate, respectively. A similar reaction has been reported, see: Devine, P. N.; Dolling, U.-H.; Heid, R. M. Jr.; Tschaen, D. M. Tetrahedron Lett. 1996, 37, 2683.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 2683
    • Devine, P.N.1    Dolling, U.-H.2    Heid Jr., R.M.3    Tschaen, D.M.4
  • 12
    • 33745701470 scopus 로고    scopus 로고
    • note
    • Initially, we tested a reagent controlled C-H insertion reaction of diazoester 13, which was readily available from 10. Utilizing several chiral rhodium catalysts, the yield and the selectivity of 14 were unsatisfactory as shown in Scheme 3.
  • 13
    • 33745715557 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra of 15, which was readily converted from 5, as shown in Scheme 4.
  • 14
    • 33745715558 scopus 로고    scopus 로고
    • note
    • The absolute configuration of 5 was determined as 2R,3R by comparing the optical rotation with that of reported compound 16, see ref. 13. Preparation of 16 from 5 was performed by a decarbonylation reaction (Schemed).
  • 20
    • 33745729499 scopus 로고    scopus 로고
    • note
    • 4 proceeded smoothly to afford 5a in 94% yield and a 43% de.
  • 21
    • 33745715561 scopus 로고    scopus 로고
    • note
    • +].
  • 22
    • 0023885338 scopus 로고
    • (a) For a pentalenolactone, see: Mori, K.; Tsuji, M. Tetrahedron 1988, 44, 2835.
    • (1988) Tetrahedron , vol.44 , pp. 2835
    • Mori, K.1    Tsuji, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.