Synthesis and reactions of 1,2-disubstituted methylenecyclopropanes prepared via intramolecular cyclopropanation of allenic diazoacetates

Tetrahedron Letters

Volumn 38, Issue 22, 1997, Pages 3833-3836

  Lautens, Mark ^a   Meyer, Christophe ^a   Van Oeveren, Arjan ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; CYCLOPROPANE DERIVATIVE; METHYLENECYCLOPROPANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 0030995583     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00765-X     Document Type: Article

References (23)

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3. (c) Binger, P.; Fox, D. In: Methods of Organic Chemistry (Houben Weyl), vol. E 21C, Part D., 1.6.1.2.3, p 2997.
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11. (k) Lautens, M.; Meyer, C.: Lorenz, A. J. Am. Chem. Soc. in press.
12. (a) Lautens, M.; Delanghe, P.H.M. J. Am. Chem. Soc. 1994, 116, 8526 and references cited therein.
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17. The allenic alcohols were prepared by conventional methods: For 1a,d,e see ref. 2. β-allenic alcohols 1b and 1f were prepared from ethyl pentadi-3,4-enoate, respectively by addition of MeMgBr, or monoreduction with DIBAL-H followed by one-pot addition of PhMgBr: (a) Brandsma, L.; Verkruijsse, H.D. Synthesis of Acetylenes, Allenes and Cumulenes; Elsevier: Amsterdam, 1981.
18. (b) Pyo, S.; Skowron III, J.F.; Cha, J.K. Tetrahedron Lett. 1992, 33, 4703. For the preparation of 1g,h,i see:
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22. This compound is contaminated by a minor by-product which might be its (Z) isomer.
23. For a review on allylic organometallics including allylstannanes, see: Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.