Diastereoselective generation of lithium carbenoid reagent RCH(OMEM)CFBrLi and its reaction with electrophiles

Masaki Shimizu; Yoko Takebe; Manabu Kuroboshi; Tamejiro Hiyama

doi:10.1016/0040-4039(96)01684-X

Diastereoselective generation of lithium carbenoid reagent RCH(OMEM)CFBrLi and its reaction with electrophiles

Masaki Shimizu, Yoko Takebe, Manabu Kuroboshi, Tamejiro Hiyama

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12 Citations (Scopus)

Abstract

Treatment of RCH(OMEM)CFBr₂ with n-BuLi at -130°C in the presence of 4-heptanone gives the corresponding adduct diastereoselectively. The stereochemical outcome is explained in terms of the chelation between lithium and oxygen atoms of the MEM group. Starting with 2-phenylpropanal, a product is produced highly selectively containing three contiguous stereocenters including a -CFBr- moiety.

Original language	English
Pages (from-to)	7387-7390
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	41
DOIs	https://doi.org/10.1016/0040-4039(96)01684-X
Publication status	Published - Oct 7 1996

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ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Shimizu, M., Takebe, Y., Kuroboshi, M., & Hiyama, T. (1996). Diastereoselective generation of lithium carbenoid reagent RCH(OMEM)CFBrLi and its reaction with electrophiles. Tetrahedron Letters, 37(41), 7387-7390. https://doi.org/10.1016/0040-4039(96)01684-X

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abstract = "Treatment of RCH(OMEM)CFBr2 with n-BuLi at -130°C in the presence of 4-heptanone gives the corresponding adduct diastereoselectively. The stereochemical outcome is explained in terms of the chelation between lithium and oxygen atoms of the MEM group. Starting with 2-phenylpropanal, a product is produced highly selectively containing three contiguous stereocenters including a -CFBr- moiety.",

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AU - Hiyama, Tamejiro

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AB - Treatment of RCH(OMEM)CFBr2 with n-BuLi at -130°C in the presence of 4-heptanone gives the corresponding adduct diastereoselectively. The stereochemical outcome is explained in terms of the chelation between lithium and oxygen atoms of the MEM group. Starting with 2-phenylpropanal, a product is produced highly selectively containing three contiguous stereocenters including a -CFBr- moiety.

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10.1016/0040-4039(96)01684-X