Silicon-directed Nazarov cyclizations. 8. Stereoelectronic control of torquoselectivity

Scott E. Denmark; Michael A. Wallace; Christopher B. Walker

doi:10.1021/jo00308a001

Silicon-directed Nazarov cyclizations. 8. Stereoelectronic control of torquoselectivity

Scott E. Denmark, Michael A. Wallace, Christopher B. Walker

Chemistry

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

Abstract

The silicon-directed Nazarov cyclization of the optically active β′-silyldivinyl ketones (+)-1 and (-)-1 proceeded with near perfect stereoselectivity. The direction of conrotatory electrocyclic ring closure was controlled by the remote silyl group such that carbon-carbon bond formation occurred in an anti S_E′ sense to the silicon electrofuge.

Original language	English (US)
Pages (from-to)	5543-5545
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	55
Issue number	21
DOIs	https://doi.org/10.1021/jo00308a001
State	Published - 1990

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Organic Chemistry

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10.1021/jo00308a001

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title = "Silicon-directed Nazarov cyclizations. 8. Stereoelectronic control of torquoselectivity",

abstract = "The silicon-directed Nazarov cyclization of the optically active β′-silyldivinyl ketones (+)-1 and (-)-1 proceeded with near perfect stereoselectivity. The direction of conrotatory electrocyclic ring closure was controlled by the remote silyl group such that carbon-carbon bond formation occurred in an anti SE′ sense to the silicon electrofuge.",

author = "Denmark, {Scott E.} and Wallace, {Michael A.} and Walker, {Christopher B.}",

year = "1990",

doi = "10.1021/jo00308a001",

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pages = "5543--5545",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "21",

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AU - Denmark, Scott E.

AU - Wallace, Michael A.

AU - Walker, Christopher B.

PY - 1990

Y1 - 1990

N2 - The silicon-directed Nazarov cyclization of the optically active β′-silyldivinyl ketones (+)-1 and (-)-1 proceeded with near perfect stereoselectivity. The direction of conrotatory electrocyclic ring closure was controlled by the remote silyl group such that carbon-carbon bond formation occurred in an anti SE′ sense to the silicon electrofuge.

AB - The silicon-directed Nazarov cyclization of the optically active β′-silyldivinyl ketones (+)-1 and (-)-1 proceeded with near perfect stereoselectivity. The direction of conrotatory electrocyclic ring closure was controlled by the remote silyl group such that carbon-carbon bond formation occurred in an anti SE′ sense to the silicon electrofuge.

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M3 - Article

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Silicon-directed Nazarov cyclizations. 8. Stereoelectronic control of torquoselectivity

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