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Issue 0, 1983
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Stereochemistry of the aldol reaction between [4-t-butyldimethylsilyloxy-5-(3-t-butyldimethylsilyloxyoct-1-enyl)cyclopent-2-enyl]ethanal and cyclopentanone enolates; a key step in the total synthesis of prostacyclin

Abstract

Reactions of lithium, boron, zirconium, and tin enolates derived from cyclopentanone with [4-t-butyldimethylsilyloxy-5-(3-t-butyldimethylsilyloxyoct-1-enyl)cyclopent-2-enyl]ethanal (6) gave mainly the 5R, 6R, and 5S, 6S(prostaglandin numbering), threo-adducts, regardless of the nature of the enolate; the highest yield of threo-products (83% of a total yield of 93%) was obtained with lithium enolate in pentane at –78 °C. In contrast, the ratio of 5R,6R to 5S,6S products was significantly affected by the nature of the enolate, ranging from ca. 1:1.3 with a boron enolate to ca. 1:3 with a tin enolate, and ca. 1:4 with a lithium enolate.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1983, 1809-1812
Article type
Paper

Stereochemistry of the aldol reaction between [4-t-butyldimethylsilyloxy-5-(3-t-butyldimethylsilyloxyoct-1-enyl)cyclopent-2-enyl]ethanal and cyclopentanone enolates; a key step in the total synthesis of prostacyclin

A. D. Baxter, S. M. Roberts, B. J. Wakefield, G. T. Woolley and R. F. Newton, J. Chem. Soc., Perkin Trans. 1, 1983, 1809
DOI: 10.1039/P19830001809

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