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

Research output: Contribution to journal › Article › peer-review

13 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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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

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.",

author = "Masaki Shimizu and Yoko Takebe and Manabu Kuroboshi and Tamejiro Hiyama",

year = "1996",

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T1 - Diastereoselective generation of lithium carbenoid reagent RCH(OMEM)CFBrLi and its reaction with electrophiles

AU - Shimizu, Masaki

AU - Takebe, Yoko

AU - Kuroboshi, Manabu

AU - Hiyama, Tamejiro

PY - 1996/10/7

Y1 - 1996/10/7

N2 - 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.

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.

UR - https://www.scopus.com/pages/publications/0030574035

UR - https://www.scopus.com/pages/publications/0030574035#tab=citedBy

U2 - 10.1016/0040-4039(96)01684-X

DO - 10.1016/0040-4039(96)01684-X

M3 - Article

AN - SCOPUS:0030574035

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SP - 7387

EP - 7390

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 41

ER -

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

Abstract

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