Intramolecular bicyclization of hydroxypentynyliodonium triflate derivatives to furnish cyclopentannelated tetrahydrofurans: The first examples of cyclopentene formation following alkoxide addition to alkynyliodonium salts

Ken S. Feldman; Michelle M. Bruendl

doi:10.1016/S0040-4039(98)00415-8

Intramolecular bicyclization of hydroxypentynyliodonium triflate derivatives to furnish cyclopentannelated tetrahydrofurans: The first examples of cyclopentene formation following alkoxide addition to alkynyliodonium salts

Ken S. Feldman, Michelle M. Bruendl

Chemistry

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13 Scopus citations

Abstract

Several hydroxyalkynyliodonium triflates can be bicyclized with KNTMS₂ to provide cyclopentannelated tetrahydrofuran derivatives in modest to good yields. The diastereoselectivity of C-H insertion by the intermediate carbene is better than that observed with the corresponding NTs analogs. Product lability and an electronic mismatch between hydroxide nucleophile and iodonium electrophile likely contribute to the modest yields.

Original language	English (US)
Pages (from-to)	2911-2914
Number of pages	4
Journal	Tetrahedron Letters
Volume	39
Issue number	19
DOIs	https://doi.org/10.1016/S0040-4039(98)00415-8
State	Published - May 7 1998

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Intramolecular bicyclization of hydroxypentynyliodonium triflate derivatives to furnish cyclopentannelated tetrahydrofurans: The first examples of cyclopentene formation following alkoxide addition to alkynyliodonium salts",

abstract = "Several hydroxyalkynyliodonium triflates can be bicyclized with KNTMS2 to provide cyclopentannelated tetrahydrofuran derivatives in modest to good yields. The diastereoselectivity of C-H insertion by the intermediate carbene is better than that observed with the corresponding NTs analogs. Product lability and an electronic mismatch between hydroxide nucleophile and iodonium electrophile likely contribute to the modest yields.",

author = "Feldman, {Ken S.} and Bruendl, {Michelle M.}",

note = "Funding Information: Acknowledgment: We thank the NIH (GM37681) for financial support.",

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doi = "10.1016/S0040-4039(98)00415-8",

language = "English (US)",

volume = "39",

pages = "2911--2914",

journal = "Tetrahedron Letters",

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Intramolecular bicyclization of hydroxypentynyliodonium triflate derivatives to furnish cyclopentannelated tetrahydrofurans: The first examples of cyclopentene formation following alkoxide addition to alkynyliodonium salts. / Feldman, Ken S.; Bruendl, Michelle M.
In: Tetrahedron Letters, Vol. 39, No. 19, 07.05.1998, p. 2911-2914.

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

TY - JOUR

T1 - Intramolecular bicyclization of hydroxypentynyliodonium triflate derivatives to furnish cyclopentannelated tetrahydrofurans

T2 - The first examples of cyclopentene formation following alkoxide addition to alkynyliodonium salts

AU - Feldman, Ken S.

AU - Bruendl, Michelle M.

N1 - Funding Information: Acknowledgment: We thank the NIH (GM37681) for financial support.

PY - 1998/5/7

Y1 - 1998/5/7

N2 - Several hydroxyalkynyliodonium triflates can be bicyclized with KNTMS2 to provide cyclopentannelated tetrahydrofuran derivatives in modest to good yields. The diastereoselectivity of C-H insertion by the intermediate carbene is better than that observed with the corresponding NTs analogs. Product lability and an electronic mismatch between hydroxide nucleophile and iodonium electrophile likely contribute to the modest yields.

AB - Several hydroxyalkynyliodonium triflates can be bicyclized with KNTMS2 to provide cyclopentannelated tetrahydrofuran derivatives in modest to good yields. The diastereoselectivity of C-H insertion by the intermediate carbene is better than that observed with the corresponding NTs analogs. Product lability and an electronic mismatch between hydroxide nucleophile and iodonium electrophile likely contribute to the modest yields.

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Intramolecular bicyclization of hydroxypentynyliodonium triflate derivatives to furnish cyclopentannelated tetrahydrofurans: The first examples of cyclopentene formation following alkoxide addition to alkynyliodonium salts

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