A novel method for the stereoselective formation of trans bicyclic ketones by way of oxidative radical cyclization

Takashi Takahashi; Satoshi Tomida; Takayuki Doi

doi:10.1055/s-1999-2686

A novel method for the stereoselective formation of trans bicyclic ketones by way of oxidative radical cyclization

Takashi Takahashi, Satoshi Tomida, Takayuki Doi

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

7 Citations (Scopus)

Abstract

The stereoselective formation of cyanohydrin 4 was achieved by radical cyclization-oxygen trapping reaction of 5 into an intramolecular acrylic nitrile moiety. The cyanohydrin was used for ring closure reaction with a tosylate, providing the bicyclic systems 1 and 2 with a trans ring fusion.

Original language	English
Pages (from-to)	644-646
Number of pages	3
Journal	Synlett
Issue number	5
DOIs	https://doi.org/10.1055/s-1999-2686
Publication status	Published - 1999 Jan 1
Externally published	Yes

Keywords

Bicyclo[4.3.0]nonan-1-one
Bicyclo[4.4.0]decan-1-one
Cyanohydrin
Intramolecular alkylation
Oxidative radical cyclization

ASJC Scopus subject areas

Organic Chemistry

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10.1055/s-1999-2686

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title = "A novel method for the stereoselective formation of trans bicyclic ketones by way of oxidative radical cyclization",

abstract = "The stereoselective formation of cyanohydrin 4 was achieved by radical cyclization-oxygen trapping reaction of 5 into an intramolecular acrylic nitrile moiety. The cyanohydrin was used for ring closure reaction with a tosylate, providing the bicyclic systems 1 and 2 with a trans ring fusion.",

keywords = "Bicyclo[4.3.0]nonan-1-one, Bicyclo[4.4.0]decan-1-one, Cyanohydrin, Intramolecular alkylation, Oxidative radical cyclization",

author = "Takashi Takahashi and Satoshi Tomida and Takayuki Doi",

year = "1999",

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doi = "10.1055/s-1999-2686",

language = "English",

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AU - Takahashi, Takashi

AU - Tomida, Satoshi

AU - Doi, Takayuki

PY - 1999/1/1

Y1 - 1999/1/1

N2 - The stereoselective formation of cyanohydrin 4 was achieved by radical cyclization-oxygen trapping reaction of 5 into an intramolecular acrylic nitrile moiety. The cyanohydrin was used for ring closure reaction with a tosylate, providing the bicyclic systems 1 and 2 with a trans ring fusion.

AB - The stereoselective formation of cyanohydrin 4 was achieved by radical cyclization-oxygen trapping reaction of 5 into an intramolecular acrylic nitrile moiety. The cyanohydrin was used for ring closure reaction with a tosylate, providing the bicyclic systems 1 and 2 with a trans ring fusion.

KW - Bicyclo[4.3.0]nonan-1-one

KW - Bicyclo[4.4.0]decan-1-one

KW - Cyanohydrin

KW - Intramolecular alkylation

KW - Oxidative radical cyclization

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ER -

A novel method for the stereoselective formation of trans bicyclic ketones by way of oxidative radical cyclization

Abstract

Keywords

ASJC Scopus subject areas

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