Diastereoselective allylations of allyl-propargyl hybrid cations: Synthesis of conjugated 1,5-dien-7-yne frameworks bearing C(4)-stereogenic centers

Teruhiko Ishikawa; Toshiaki Aikawa; Yumiko Mori; Seiki Saito

doi:10.1021/ol049847g

Diastereoselective allylations of allyl-propargyl hybrid cations: Synthesis of conjugated 1,5-dien-7-yne frameworks bearing C(4)-stereogenic centers

Teruhiko Ishikawa, Toshiaki Aikawa, Yumiko Mori, Seiki Saito

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

15 Citations (Scopus)

Abstract

Chiral C(4)-substituted (E)- or (Z)-1-alkynyl-1-trimethylsilyloxy-2-butene systems provide anti-(Z) or syn-(Z) conjugated dienyne, with a very high level of stereocontrol, on treatment with BF₃·OEt₂ in CH₂Cl₂ at -50°C in the presence of allyltrimethylsilane. The Cieplak conformation for (Z)-substrates and neighboring-group participation for (2)-substrates are considered to be responsible for the stereochemical consequences.

Original language	English
Pages (from-to)	1369-1372
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	9
DOIs	https://doi.org/10.1021/ol049847g
Publication status	Published - Apr 29 2004

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol049847g

Cite this

@article{3bcdde0898614e7093961a5fc44c29e9,

title = "Diastereoselective allylations of allyl-propargyl hybrid cations: Synthesis of conjugated 1,5-dien-7-yne frameworks bearing C(4)-stereogenic centers",

abstract = "Chiral C(4)-substituted (E)- or (Z)-1-alkynyl-1-trimethylsilyloxy-2-butene systems provide anti-(Z) or syn-(Z) conjugated dienyne, with a very high level of stereocontrol, on treatment with BF3·OEt2 in CH2Cl2 at -50°C in the presence of allyltrimethylsilane. The Cieplak conformation for (Z)-substrates and neighboring-group participation for (2)-substrates are considered to be responsible for the stereochemical consequences.",

author = "Teruhiko Ishikawa and Toshiaki Aikawa and Yumiko Mori and Seiki Saito",

year = "2004",

month = apr,

day = "29",

doi = "10.1021/ol049847g",

language = "English",

volume = "6",

pages = "1369--1372",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

T1 - Diastereoselective allylations of allyl-propargyl hybrid cations

T2 - Synthesis of conjugated 1,5-dien-7-yne frameworks bearing C(4)-stereogenic centers

AU - Ishikawa, Teruhiko

AU - Aikawa, Toshiaki

AU - Mori, Yumiko

AU - Saito, Seiki

PY - 2004/4/29

Y1 - 2004/4/29

N2 - Chiral C(4)-substituted (E)- or (Z)-1-alkynyl-1-trimethylsilyloxy-2-butene systems provide anti-(Z) or syn-(Z) conjugated dienyne, with a very high level of stereocontrol, on treatment with BF3·OEt2 in CH2Cl2 at -50°C in the presence of allyltrimethylsilane. The Cieplak conformation for (Z)-substrates and neighboring-group participation for (2)-substrates are considered to be responsible for the stereochemical consequences.

AB - Chiral C(4)-substituted (E)- or (Z)-1-alkynyl-1-trimethylsilyloxy-2-butene systems provide anti-(Z) or syn-(Z) conjugated dienyne, with a very high level of stereocontrol, on treatment with BF3·OEt2 in CH2Cl2 at -50°C in the presence of allyltrimethylsilane. The Cieplak conformation for (Z)-substrates and neighboring-group participation for (2)-substrates are considered to be responsible for the stereochemical consequences.

UR - http://www.scopus.com/inward/record.url?scp=2442432587&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=2442432587&partnerID=8YFLogxK

U2 - 10.1021/ol049847g

DO - 10.1021/ol049847g

M3 - Article

C2 - 15101744

AN - SCOPUS:2442432587

SN - 1523-7060

VL - 6

SP - 1369

EP - 1372

JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Diastereoselective allylations of allyl-propargyl hybrid cations: Synthesis of conjugated 1,5-dien-7-yne frameworks bearing C(4)-stereogenic centers

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this