Seebach's conjunctive reagent enables double cyclizations

Brent D. Chandler; Jason T. Roland; Yukai Li; Erik J. Sorensen

doi:10.1021/ol100845z

Seebach's conjunctive reagent enables double cyclizations

Brent D. Chandler, Jason T. Roland, Yukai Li, Erik J. Sorensen

Chemistry

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

14 Scopus citations

Abstract

(Figure presented) When ketones flanked on both sides by nucleophilic atoms react with Seebach's nitropropenyl pivaloate reagent, direct couplings take place to give two new ring systems and three bonds. Cis-ring fusions are observed in unions leading to 5,5-, 5,6-, and 6,6-bicycles. Densely functionalized and rigid frameworks may be rapidly formed by the chemistry described herein.

Original language	English (US)
Pages (from-to)	2746-2749
Number of pages	4
Journal	Organic letters
Volume	12
Issue number	12
DOIs	https://doi.org/10.1021/ol100845z
State	Published - Jun 18 2010

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol100845z

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title = "Seebach's conjunctive reagent enables double cyclizations",

abstract = "(Figure presented) When ketones flanked on both sides by nucleophilic atoms react with Seebach's nitropropenyl pivaloate reagent, direct couplings take place to give two new ring systems and three bonds. Cis-ring fusions are observed in unions leading to 5,5-, 5,6-, and 6,6-bicycles. Densely functionalized and rigid frameworks may be rapidly formed by the chemistry described herein.",

author = "Chandler, {Brent D.} and Roland, {Jason T.} and Yukai Li and Sorensen, {Erik J.}",

year = "2010",

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doi = "10.1021/ol100845z",

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journal = "Organic letters",

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T1 - Seebach's conjunctive reagent enables double cyclizations

AU - Chandler, Brent D.

AU - Roland, Jason T.

AU - Li, Yukai

AU - Sorensen, Erik J.

PY - 2010/6/18

Y1 - 2010/6/18

N2 - (Figure presented) When ketones flanked on both sides by nucleophilic atoms react with Seebach's nitropropenyl pivaloate reagent, direct couplings take place to give two new ring systems and three bonds. Cis-ring fusions are observed in unions leading to 5,5-, 5,6-, and 6,6-bicycles. Densely functionalized and rigid frameworks may be rapidly formed by the chemistry described herein.

AB - (Figure presented) When ketones flanked on both sides by nucleophilic atoms react with Seebach's nitropropenyl pivaloate reagent, direct couplings take place to give two new ring systems and three bonds. Cis-ring fusions are observed in unions leading to 5,5-, 5,6-, and 6,6-bicycles. Densely functionalized and rigid frameworks may be rapidly formed by the chemistry described herein.

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DO - 10.1021/ol100845z

M3 - Article

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JO - Organic letters

JF - Organic letters

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ER -

Seebach's conjunctive reagent enables double cyclizations

Abstract

All Science Journal Classification (ASJC) codes

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