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Highly stereoselective intramolecular alkylation of ester enolate: An approach to trans-hydrindane system

✍ Scribed by Soon Hyuk Ahn; Deukjoon Kim; Moon Woo Chun; Won-Keun Chung

Publisher: Elsevier Science
Year: 1986
Tongue: French
Weight: 184 KB
Volume: 27
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)84144-1

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✦ Synopsis

Sumary: Highly diastereoselective intramolecular alkylation of acyclic ester system was developed based upon allylic strain concept as an approach to tram-hydrindane system.

Stereoselective construction of trans-hydrindane nucleus has been a continuous challenge to synthetic organic chemists.' In connection with our studies on synthesis of optically active steroid CD ring, we have envisioned that intramolecular alkylation of ester such as 1 would provide cyclohexanecarboxylate 3 in a stereoselective manner through a conformation 2 where allylic hydrogen and OR (or ON) group are eclipsed:' Straightforward elaboration of functional groups in compound 3 would lead to trans-hydrindane 4 . Very recently Fleming, Koga, Yamamto, and McGarvey reported successful cases of diastereoselective alkylation of acyclic esters with chirality at beta position during the course of our work.2 X Me

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