Homochiral Ketals in Organic Synthesis. Enantioselective Synthesis of (R)-Muscone

Keith A. Nelson; Eugene A. Mash

doi:10.1021/jo00364a019

Homochiral Ketals in Organic Synthesis. Enantioselective Synthesis of (R)-Muscone

Keith A. Nelson, Eugene A. Mash

Chemistry and Biochemistry

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

61 Scopus citations

Abstract

An efficient, enantioselective preparation of (R)-muscone employing a diastereoselective Simmons-Smith cyclopropanation is described. Cyclopropanation is directed via chelation control by a homochiral ketal protecting group derived from unnatural tartaric acid. The overall yield of (R)-muscone (>95% R) from commercially available cyclopentadecanone is 60% over seven steps.

Original language	English (US)
Pages (from-to)	2721-2724
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	51
Issue number	14
DOIs	https://doi.org/10.1021/jo00364a019
State	Published - 1986

ASJC Scopus subject areas

Organic Chemistry

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title = "Homochiral Ketals in Organic Synthesis. Enantioselective Synthesis of (R)-Muscone",

abstract = "An efficient, enantioselective preparation of (R)-muscone employing a diastereoselective Simmons-Smith cyclopropanation is described. Cyclopropanation is directed via chelation control by a homochiral ketal protecting group derived from unnatural tartaric acid. The overall yield of (R)-muscone (>95\% R) from commercially available cyclopentadecanone is 60\% over seven steps.",

author = "Nelson, \{Keith A.\} and Mash, \{Eugene A.\}",

year = "1986",

doi = "10.1021/jo00364a019",

language = "English (US)",

volume = "51",

pages = "2721--2724",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "14",

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TY - JOUR

T1 - Homochiral Ketals in Organic Synthesis. Enantioselective Synthesis of (R)-Muscone

AU - Nelson, Keith A.

AU - Mash, Eugene A.

PY - 1986

Y1 - 1986

N2 - An efficient, enantioselective preparation of (R)-muscone employing a diastereoselective Simmons-Smith cyclopropanation is described. Cyclopropanation is directed via chelation control by a homochiral ketal protecting group derived from unnatural tartaric acid. The overall yield of (R)-muscone (>95% R) from commercially available cyclopentadecanone is 60% over seven steps.

AB - An efficient, enantioselective preparation of (R)-muscone employing a diastereoselective Simmons-Smith cyclopropanation is described. Cyclopropanation is directed via chelation control by a homochiral ketal protecting group derived from unnatural tartaric acid. The overall yield of (R)-muscone (>95% R) from commercially available cyclopentadecanone is 60% over seven steps.

UR - https://www.scopus.com/pages/publications/33845374391

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U2 - 10.1021/jo00364a019

DO - 10.1021/jo00364a019

M3 - Article

AN - SCOPUS:33845374391

SN - 0022-3263

VL - 51

SP - 2721

EP - 2724

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 14

ER -

Homochiral Ketals in Organic Synthesis. Enantioselective Synthesis of (R)-Muscone

Abstract

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