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Volumn 74, Issue 21, 2009, Pages 8261-8271

Nonracemic bicyclic lactam lactones via regio- and cis-diastereocontrolled C-H insertion. Asymmetric synthesis of (8S,8aS)-octahydroindolizidin-8-ol and (1S,8aS)-octahydroindolizidin-1-ol

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC SYNTHESIS; BICYCLIC LACTAMS; C-H INSERTION; CHEMICAL EQUATIONS; CHIRAL BUILDING BLOCKS; DIASTEREO-SELECTIVITY; GOOD YIELD; PYRROLIDIN-2-ONES;

EID: 70350728714     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901790g     Document Type: Article
Times cited : (33)

References (81)
  • 38
    • 0020577909 scopus 로고
    • N,O-Dibenzylation of rac-1, see
    • (b) N,O-Dibenzylation of rac-1, see: Herdeis, C. Arch. Pharm. 1983, 316, 719.
    • (1983) Arch. Pharm. , vol.316 , pp. 719
    • Herdeis, C.1
  • 44
    • 70350711573 scopus 로고    scopus 로고
    • Purchased from Sigma Aldrich Chemical Co., USA
    • (a) Purchased from Sigma Aldrich Chemical Co., USA.
  • 50
    • 70350735259 scopus 로고    scopus 로고
    • note
    • 2) to that used for (S)-8.We found that the yields of the C-H insertion products Ba,b are markedly lower, and ether products Ca,b were also obtained. The dimer Db was also formed in the reaction of Ab but was not detected in the reaction of Aa.
  • 52
    • 70350702100 scopus 로고    scopus 로고
    • note
    • f (equatorial)=-32.164 kcal/mol.
  • 62
    • 70350727834 scopus 로고    scopus 로고
    • note
    • 1H NMR of this complex is identical to that reported (see Supporting Information).
  • 74
    • 70350704088 scopus 로고    scopus 로고
    • note
    • 3, 300 MHz) δ 7.78-7.90 (m, 2 H), 7.52-7.68 (m, 3 H), 7.15-7.35 (m, 5 H), 6.78 (ddd, J=15.1, 7.2, 7.2 Hz, 1 H), 6.25 (d, J=15.1 Hz, 1 H), 5.27-5.31 (m, 1 H), 4.88 (d, J=15.0 Hz, 1 H), 4.02 (d, J=15.2 Hz, 1 H), 3.78-3.86 (m, 1 H), 2.78 (dd, J=17.4, 7.5 Hz, 1 H), 2.50 (dd, J=17.7, 5.4 Hz, 1 H), 1.95-2.12 (m, 2 H),1.93 (s, 3 H). The characteristic resonances of the hydrogens of the vinylic sulfone occurred at δ 6.25 (d, J=15.1 Hz, 1H) and δ 6.78 (ddd, J=15.1, 7.2, 7.2 Hz, 1 H).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.