The first In(OTf)3-catalyzed conversion of kinetically formed homoallylic alcohols into the thermodynamically preferred regioisomers: Application to the synthesis of 22α-sterols

Teck Peng Loh; Kui Thong Tan; Qi Ying Hu

doi:10.1002/1521-3773(20010803)40:15<2921::AID-ANIE2921>3.0.CO;2-V

The first In(OTf)₃-catalyzed conversion of kinetically formed homoallylic alcohols into the thermodynamically preferred regioisomers: Application to the synthesis of 22α-sterols

Teck Peng Loh^*, Kui Thong Tan, Qi Ying Hu

^*Corresponding author for this work

National University of Singapore

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

61 Citations (Scopus)

Abstract

A retro-ene reaction that generates the parent aldehyde and a sigmatropic rearrangement are involved in the In(OTf)₃-catalyzed conversion of homoallylic alcohols 1 into the thermodynamically favored regioisomers 2. This method can be used for the stereocontrolled synthesis of linear homoallylic 22α-sterols from their readily accessible branched 22β isomers.

Original language	English
Pages (from-to)	2921-2922
Number of pages	2
Journal	Angewandte Chemie - International Edition
Volume	40
Issue number	15
DOIs	https://doi.org/10.1002/1521-3773(20010803)40:15<2921::AID-ANIE2921>3.0.CO;2-V
Publication status	Published - Aug 3 2001
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

Ene reaction
Indium
Retro reactions
Sigmatropic rearrangement

Access to Document

10.1002/1521-3773(20010803)40:15<2921::AID-ANIE2921>3.0.CO;2-V

Cite this

@article{373915404e0440469e4c5034bdbfefa8,

title = "The first In(OTf)3-catalyzed conversion of kinetically formed homoallylic alcohols into the thermodynamically preferred regioisomers: Application to the synthesis of 22α-sterols",

abstract = "A retro-ene reaction that generates the parent aldehyde and a sigmatropic rearrangement are involved in the In(OTf)3-catalyzed conversion of homoallylic alcohols 1 into the thermodynamically favored regioisomers 2. This method can be used for the stereocontrolled synthesis of linear homoallylic 22α-sterols from their readily accessible branched 22β isomers.",

keywords = "Ene reaction, Indium, Retro reactions, Sigmatropic rearrangement",

author = "Loh, {Teck Peng} and Tan, {Kui Thong} and Hu, {Qi Ying}",

year = "2001",

month = aug,

day = "3",

doi = "10.1002/1521-3773(20010803)40:15<2921::AID-ANIE2921>3.0.CO;2-V",

language = "English",

volume = "40",

pages = "2921--2922",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "15",

}

The first In(OTf)₃-catalyzed conversion of kinetically formed homoallylic alcohols into the thermodynamically preferred regioisomers: Application to the synthesis of 22α-sterols. / Loh, Teck Peng; Tan, Kui Thong; Hu, Qi Ying.
In: Angewandte Chemie - International Edition, Vol. 40, No. 15, 03.08.2001, p. 2921-2922.

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

TY - JOUR

T1 - The first In(OTf)3-catalyzed conversion of kinetically formed homoallylic alcohols into the thermodynamically preferred regioisomers

T2 - Application to the synthesis of 22α-sterols

AU - Loh, Teck Peng

AU - Tan, Kui Thong

AU - Hu, Qi Ying

PY - 2001/8/3

Y1 - 2001/8/3

N2 - A retro-ene reaction that generates the parent aldehyde and a sigmatropic rearrangement are involved in the In(OTf)3-catalyzed conversion of homoallylic alcohols 1 into the thermodynamically favored regioisomers 2. This method can be used for the stereocontrolled synthesis of linear homoallylic 22α-sterols from their readily accessible branched 22β isomers.

AB - A retro-ene reaction that generates the parent aldehyde and a sigmatropic rearrangement are involved in the In(OTf)3-catalyzed conversion of homoallylic alcohols 1 into the thermodynamically favored regioisomers 2. This method can be used for the stereocontrolled synthesis of linear homoallylic 22α-sterols from their readily accessible branched 22β isomers.

KW - Ene reaction

KW - Indium

KW - Retro reactions

KW - Sigmatropic rearrangement

UR - http://www.scopus.com/inward/record.url?scp=0035800355&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035800355&partnerID=8YFLogxK

U2 - 10.1002/1521-3773(20010803)40:15<2921::AID-ANIE2921>3.0.CO;2-V

DO - 10.1002/1521-3773(20010803)40:15<2921::AID-ANIE2921>3.0.CO;2-V

M3 - Article

AN - SCOPUS:0035800355

SN - 1433-7851

VL - 40

SP - 2921

EP - 2922

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 15

ER -