Highly diastereoselective preparation of cyclic sulfates from allyl and homoallyl alcohols via one-pot halocyclosulfations

Masahiro Inoue; Shinji Motomatsu; Masahisa Nakada

doi:10.1081/SCC-120022175

Highly diastereoselective preparation of cyclic sulfates from allyl and homoallyl alcohols via one-pot halocyclosulfations

Masahiro Inoue, Shinji Motomatsu, Masahisa Nakada^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

3 Citations (Scopus)

Abstract

Diastereoselective electrophilic heteroatom cyclizations of the monosulfates of homoallyl and allyl alcohols are described. This cyclization tends to afford thermodynamically favored products, and high 1,3-asymmetric induction is observed in the case of homoallyl alcohols.

Original language	English
Pages (from-to)	2857-2866
Number of pages	10
Journal	Synthetic Communications
Volume	33
Issue number	16
DOIs	https://doi.org/10.1081/SCC-120022175
Publication status	Published - 2003

Keywords

Allyl alcohol
Asymmetric induction
Cyclic sulfate
Halocyclosulfation
Homoallyl alcohol

ASJC Scopus subject areas

Organic Chemistry

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10.1081/SCC-120022175

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title = "Highly diastereoselective preparation of cyclic sulfates from allyl and homoallyl alcohols via one-pot halocyclosulfations",

abstract = "Diastereoselective electrophilic heteroatom cyclizations of the monosulfates of homoallyl and allyl alcohols are described. This cyclization tends to afford thermodynamically favored products, and high 1,3-asymmetric induction is observed in the case of homoallyl alcohols.",

keywords = "Allyl alcohol, Asymmetric induction, Cyclic sulfate, Halocyclosulfation, Homoallyl alcohol",

author = "Masahiro Inoue and Shinji Motomatsu and Masahisa Nakada",

note = "Funding Information: This work was supported in part by Waseda University Grant for Special Research Projects (Individual Research). We thank Dr. Motoo Shiro of Rigaku X-Ray Research Laboratory for the X-ray crystal structure determination of 2a(syn).",

year = "2003",

doi = "10.1081/SCC-120022175",

language = "English",

volume = "33",

pages = "2857--2866",

journal = "Synthetic Communications",

issn = "0039-7911",

publisher = "Taylor and Francis Ltd.",

number = "16",

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TY - JOUR

T1 - Highly diastereoselective preparation of cyclic sulfates from allyl and homoallyl alcohols via one-pot halocyclosulfations

AU - Inoue, Masahiro

AU - Motomatsu, Shinji

AU - Nakada, Masahisa

N1 - Funding Information: This work was supported in part by Waseda University Grant for Special Research Projects (Individual Research). We thank Dr. Motoo Shiro of Rigaku X-Ray Research Laboratory for the X-ray crystal structure determination of 2a(syn).

PY - 2003

Y1 - 2003

N2 - Diastereoselective electrophilic heteroatom cyclizations of the monosulfates of homoallyl and allyl alcohols are described. This cyclization tends to afford thermodynamically favored products, and high 1,3-asymmetric induction is observed in the case of homoallyl alcohols.

AB - Diastereoselective electrophilic heteroatom cyclizations of the monosulfates of homoallyl and allyl alcohols are described. This cyclization tends to afford thermodynamically favored products, and high 1,3-asymmetric induction is observed in the case of homoallyl alcohols.

KW - Allyl alcohol

KW - Asymmetric induction

KW - Cyclic sulfate

KW - Halocyclosulfation

KW - Homoallyl alcohol

UR - http://www.scopus.com/inward/record.url?scp=0042630993&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0042630993&partnerID=8YFLogxK

U2 - 10.1081/SCC-120022175

DO - 10.1081/SCC-120022175

M3 - Article

AN - SCOPUS:0042630993

SN - 0039-7911

VL - 33

SP - 2857

EP - 2866

JO - Synthetic Communications

JF - Synthetic Communications

IS - 16

ER -

Highly diastereoselective preparation of cyclic sulfates from allyl and homoallyl alcohols via one-pot halocyclosulfations

Abstract

Keywords

ASJC Scopus subject areas

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