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

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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/0040-4039(96)01684-X

Fingerprint Dive into the research topics of 'Diastereoselective generation of lithium carbenoid reagent RCH(OMEM)CFBrLi and its reaction with electrophiles'. Together they form a unique fingerprint.

Cite this

@article{52e89e3225604e94b82a4e95d53ee31e,

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",

month = oct,

day = "7",

doi = "10.1016/0040-4039(96)01684-X",

language = "English",

volume = "37",

pages = "7387--7390",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "41",

}

TY - JOUR

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 - http://www.scopus.com/inward/record.url?scp=0030574035&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0030574035&partnerID=8YFLogxK

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

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

M3 - Article

AN - SCOPUS:0030574035

VL - 37

SP - 7387

EP - 7390

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 41

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Cite this