Triflic acid catalyzed synthesis of spirocycles via acetylene cations

Tienan Jin; Masafumi Himuro; Yoshinori Yamamoto

doi:10.1002/anie.200901771

Triflic acid catalyzed synthesis of spirocycles via acetylene cations

Tienan Jin, Masafumi Himuro, Yoshinori Yamamoto

SCI - Research and Analytical Center for Giant Molecules

Tohoku University

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

66 Citations (Scopus)

Abstract

Rings of various shapes and sizes: Spirocyclic hydrocarbons 2 were obtained in good to excellent yield through the triflic acid (TfOH) catalyzed cyclization of alkynyl-substituted cyclic tertiary alcohols 1 under mild conditions with good control of ring size (see scheme). The method was extended to the synthesis of bridged bicyclic ketones with high stereoselectivity.

Original language	English
Pages (from-to)	5893-5896
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	48
Issue number	32
DOIs	https://doi.org/10.1002/anie.200901771
Publication status	Published - 2009 Jul 27

Keywords

Alkynes
Cyclization
Spirocycles
Tertiary alcohols
Triflic acid

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10.1002/anie.200901771

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title = "Triflic acid catalyzed synthesis of spirocycles via acetylene cations",

abstract = "Rings of various shapes and sizes: Spirocyclic hydrocarbons 2 were obtained in good to excellent yield through the triflic acid (TfOH) catalyzed cyclization of alkynyl-substituted cyclic tertiary alcohols 1 under mild conditions with good control of ring size (see scheme). The method was extended to the synthesis of bridged bicyclic ketones with high stereoselectivity.",

keywords = "Alkynes, Cyclization, Spirocycles, Tertiary alcohols, Triflic acid",

author = "Tienan Jin and Masafumi Himuro and Yoshinori Yamamoto",

year = "2009",

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T1 - Triflic acid catalyzed synthesis of spirocycles via acetylene cations

AU - Jin, Tienan

AU - Himuro, Masafumi

AU - Yamamoto, Yoshinori

PY - 2009/7/27

Y1 - 2009/7/27

N2 - Rings of various shapes and sizes: Spirocyclic hydrocarbons 2 were obtained in good to excellent yield through the triflic acid (TfOH) catalyzed cyclization of alkynyl-substituted cyclic tertiary alcohols 1 under mild conditions with good control of ring size (see scheme). The method was extended to the synthesis of bridged bicyclic ketones with high stereoselectivity.

AB - Rings of various shapes and sizes: Spirocyclic hydrocarbons 2 were obtained in good to excellent yield through the triflic acid (TfOH) catalyzed cyclization of alkynyl-substituted cyclic tertiary alcohols 1 under mild conditions with good control of ring size (see scheme). The method was extended to the synthesis of bridged bicyclic ketones with high stereoselectivity.

KW - Alkynes

KW - Cyclization

KW - Spirocycles

KW - Tertiary alcohols

KW - Triflic acid

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DO - 10.1002/anie.200901771

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 32

ER -

Triflic acid catalyzed synthesis of spirocycles via acetylene cations

Abstract

Keywords

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