Diastereoselective cyclopropanation via homochiral ketals. Dioxolane structural effects

Eugene A. Mash; Keith A. Nelson; Phillip C. Heidt

doi:10.1016/S0040-4039(00)95995-1

Diastereoselective cyclopropanation via homochiral ketals. Dioxolane structural effects

Eugene A. Mash, Keith A. Nelson, Phillip C. Heidt

Chemistry and Biochemistry

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

22 Scopus citations

Abstract

A series of 2-cyclohexen-1-one ketals related to 2-cyclohexen-1-one 1,4-di- O-benzyl-L-threitol ketal but possesing different dioxolane appendages was prepared and subjected to Simmons-Smith cycloproponation. The observed diastereoselectivity decreased when oxygen was present in the appendages. In the absence of appendage oxygen, the sense of the observed diastereoselectivity was found to depend upon dioxolane chirality. The amount of diastereoselectivity observed was remarkably independent of the nature of the appendages.

Original language	English (US)
Pages (from-to)	1865-1868
Number of pages	4
Journal	Tetrahedron Letters
Volume	28
Issue number	17
DOIs	https://doi.org/10.1016/S0040-4039(00)95995-1
State	Published - 1987

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)95995-1

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title = "Diastereoselective cyclopropanation via homochiral ketals. Dioxolane structural effects",

abstract = "A series of 2-cyclohexen-1-one ketals related to 2-cyclohexen-1-one 1,4-di- O-benzyl-L-threitol ketal but possesing different dioxolane appendages was prepared and subjected to Simmons-Smith cycloproponation. The observed diastereoselectivity decreased when oxygen was present in the appendages. In the absence of appendage oxygen, the sense of the observed diastereoselectivity was found to depend upon dioxolane chirality. The amount of diastereoselectivity observed was remarkably independent of the nature of the appendages.",

author = "Mash, {Eugene A.} and Nelson, {Keith A.} and Heidt, {Phillip C.}",

note = "Funding Information: Acknowledgement is made to the donors of The Petroleum Research Fund, administered by The American Chemical Society, for support of this research. Partial support of this research by Research Corporation, by The American Cancer Society, and by the American Heart ASSOciation, Arizona Affiliate, is gratefully acknowledged.",

year = "1987",

doi = "10.1016/S0040-4039(00)95995-1",

language = "English (US)",

volume = "28",

pages = "1865--1868",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

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T1 - Diastereoselective cyclopropanation via homochiral ketals. Dioxolane structural effects

AU - Mash, Eugene A.

AU - Nelson, Keith A.

AU - Heidt, Phillip C.

N1 - Funding Information: Acknowledgement is made to the donors of The Petroleum Research Fund, administered by The American Chemical Society, for support of this research. Partial support of this research by Research Corporation, by The American Cancer Society, and by the American Heart ASSOciation, Arizona Affiliate, is gratefully acknowledged.

PY - 1987

Y1 - 1987

N2 - A series of 2-cyclohexen-1-one ketals related to 2-cyclohexen-1-one 1,4-di- O-benzyl-L-threitol ketal but possesing different dioxolane appendages was prepared and subjected to Simmons-Smith cycloproponation. The observed diastereoselectivity decreased when oxygen was present in the appendages. In the absence of appendage oxygen, the sense of the observed diastereoselectivity was found to depend upon dioxolane chirality. The amount of diastereoselectivity observed was remarkably independent of the nature of the appendages.

AB - A series of 2-cyclohexen-1-one ketals related to 2-cyclohexen-1-one 1,4-di- O-benzyl-L-threitol ketal but possesing different dioxolane appendages was prepared and subjected to Simmons-Smith cycloproponation. The observed diastereoselectivity decreased when oxygen was present in the appendages. In the absence of appendage oxygen, the sense of the observed diastereoselectivity was found to depend upon dioxolane chirality. The amount of diastereoselectivity observed was remarkably independent of the nature of the appendages.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 17

ER -

Diastereoselective cyclopropanation via homochiral ketals. Dioxolane structural effects

Abstract

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