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A short, stereospecific route to chiral trans-2,6-disubstituted quinuclidines

โœ Scribed by E.J Corey; Po-wai Yuen

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
230 KB
Volume
30
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

An efficient six-step stereospecific synthesis of trans-2,Gdiphenylquinuclidine (1) is described together with an effective resolution of 1 into pure enantiomers. A key step in the synthesis is a highly efficient, catalyzed Diels-Alder reaction.

Although the quinuclidine ring is an important structural subunit in numerous biologically active synthetic compounds and several important alkaloids (e.g. ajmaline, cinchonine, quinine, quinidine, and sarpagine), almost all known syntheses of this system follow long-known, classical r0utes.l This paper describes a short and stereospecific route to 2,6_disubstituted quinuclidines which is based on a novel Diels-Alder construction, specifically leading to rruns-2,6diphenylquinuclidine

(1). An efficient resolution of

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