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Volumn 25, Issue 2, 1986, Pages 160-162

α‐Deprotonation of an α‐Chiral 2‐Alkenylcarbamate with Retention and Lithium‐Titanium Exchange with Inversion— the Homoaldol Reaction with 1,3‐Chirality Transfer

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Indexed keywords


EID: 84985580890     PISSN: 05700833     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.198601601     Document Type: Article
Times cited : (75)

References (41)
  • 7
    • 0000163012 scopus 로고
    • Die Homoaldol-Reaktion oder wie man Probleme der Regio- und Stereoselektivität in den Griff bekommt
    • (a) Review
    • (1984) Angewandte Chemie , vol.96 , pp. 930
    • Hoppe, D.1
  • 10
    • 84985512177 scopus 로고    scopus 로고
    • 19F‐NMR spectroscopy [4d].
  • 14
    • 84985571198 scopus 로고    scopus 로고
    • 3).
  • 15
    • 84985529630 scopus 로고    scopus 로고
    • F = 0.48 (0.40), ether/petroleum ether (1:1).
  • 16
    • 84985571188 scopus 로고    scopus 로고
    • Corrected values, based on enantiomerically pure (−)‐5.
  • 17
    • 84985522227 scopus 로고    scopus 로고
    • 3OH).
  • 20
    • 84970549066 scopus 로고
    • Organotitanium reagents in organic synthesis a simple means to adjust reactivity and selectivity of carbanions
    • Reviews
    • (1982) Top. Curr. Chem. , vol.106 , pp. 1
    • Reetz, M.T.1
  • 23
    • 84985585297 scopus 로고    scopus 로고
    • Reaction conditions: (1) (+)‐8b (30% ee), acetic anhydride, triethylamine, 10 mol‐% 4‐(dimethylamino)pyridine
  • 24
    • 84985522249 scopus 로고    scopus 로고
    • 3, 1.0 equiv. methanesulfonic acid in methanol/dichloromethane, −70 to −20°C; dimethyl sulfide
  • 25
    • 84985523505 scopus 로고    scopus 로고
    • 4/tetrahydrofuran, 0°C.–(−)‐11: [α] D24 −1.05 (c = 2.4, ethanol), 17% ee [12].
  • 29
    • 84985632260 scopus 로고    scopus 로고
    • 4 (isopropanol, 20°C), gave (−)‐8a ([α] D24 − 1.55), 19% ee (corrected [7] 25% ee), along with (−)‐9a (59:41). Therefore, (−)‐9a must have at least the same enantiomeric purity.
  • 30
    • 84985605541 scopus 로고    scopus 로고
    • The asymmetric induction cannot be due to chiral associates (e.g., rac‐6·R)‐5 or rac‐10·(R)‐5 since similar results are obtained with completely deprotonated carbamates (e.g., starting from R)‐5, ethyl instead of isobutyl.
  • 37
    • 84985502144 scopus 로고    scopus 로고
    • Note the change of CIP priorities.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.