Multicomponent reactions: Synthesis of spirocyclic tetrahydropyran derivatives by prins cyclization

Arun K. Ghosh; Dongwoo Shin; Gary Schiltz

doi:10.3987/com-02-s(m)63

Multicomponent reactions: Synthesis of spirocyclic tetrahydropyran derivatives by prins cyclization

Arun K. Ghosh^*, Dongwoo Shin, Gary Schiltz

^*Corresponding author for this work

Chemistry

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

15 Scopus citations

Abstract

Substituted spirocyclic tetrahydropyranyl mesylates and tosylates have been synthesized in good yields using a Prins-type cyclization of various cyclic ketones, a homoallylic alcohol and either methanesulfonic or p-toluenesulfonic acid under non-aqueous conditions. The mesylates thus produced could then be transformed into the corresponding Boc-protected amines using an efficient two step procedure.

Original language	English (US)
Pages (from-to)	659-666
Number of pages	8
Journal	Heterocycles
Volume	58
DOIs	https://doi.org/10.3987/com-02-s(m)63
State	Published - Nov 22 2002

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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abstract = "Substituted spirocyclic tetrahydropyranyl mesylates and tosylates have been synthesized in good yields using a Prins-type cyclization of various cyclic ketones, a homoallylic alcohol and either methanesulfonic or p-toluenesulfonic acid under non-aqueous conditions. The mesylates thus produced could then be transformed into the corresponding Boc-protected amines using an efficient two step procedure.",

author = "Ghosh, {Arun K.} and Dongwoo Shin and Gary Schiltz",

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doi = "10.3987/com-02-s(m)63",

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T1 - Multicomponent reactions

T2 - Synthesis of spirocyclic tetrahydropyran derivatives by prins cyclization

AU - Ghosh, Arun K.

AU - Shin, Dongwoo

AU - Schiltz, Gary

PY - 2002/11/22

Y1 - 2002/11/22

N2 - Substituted spirocyclic tetrahydropyranyl mesylates and tosylates have been synthesized in good yields using a Prins-type cyclization of various cyclic ketones, a homoallylic alcohol and either methanesulfonic or p-toluenesulfonic acid under non-aqueous conditions. The mesylates thus produced could then be transformed into the corresponding Boc-protected amines using an efficient two step procedure.

AB - Substituted spirocyclic tetrahydropyranyl mesylates and tosylates have been synthesized in good yields using a Prins-type cyclization of various cyclic ketones, a homoallylic alcohol and either methanesulfonic or p-toluenesulfonic acid under non-aqueous conditions. The mesylates thus produced could then be transformed into the corresponding Boc-protected amines using an efficient two step procedure.

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U2 - 10.3987/com-02-s(m)63

DO - 10.3987/com-02-s(m)63

M3 - Article

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EP - 666

JO - Heterocycles

JF - Heterocycles

ER -

Multicomponent reactions: Synthesis of spirocyclic tetrahydropyran derivatives by prins cyclization

Abstract

ASJC Scopus subject areas

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