Development of Highly Stereoselective and Regioselective Reactions Based on the Alkyne-Co2(CO)6 Complexes

Chisato Mukai; Miyoji Hanaoka

doi:10.1055/s-1996-5301

Synlett 1996; 1996(1): 11-17
DOI: 10.1055/s-1996-5301

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Development of Highly Stereoselective and Regioselective Reactions Based on the Alkyne-Co₂(CO)₆ Complexes

Chisato Mukai^* , Miyoji Hanaoka¹

^*Faculty of Pharmaceutical Sciences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920, Japan, Telephone: +81-762-34-4450; Fax: +81-762-33-7414

Abstract

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Highly syn-selective aldol reaction of the propynal-Co₂(CO)₆ complexes with silyl enol nucleophiles under the Mukaiyama conditions was developed. Based on the newly developed stereoselective reactions, we have succeeded in stereoselective syntheses of (±)-PS-5, (±)-blastmycinone, and (+)-bengamide E. On the second half in this Account, we describe the novel endo mode ring closure of the epoxy-alcohols via the corresponding cobalt complexes. In this cyclization, complete regioselectivity was attained and the reaction proceeded with retention of configuration at the propynyl position of tetrahydropyran and tetrahydrofuran derivatives.

alkyne-Co₂(CO)₆ complex - aldol reaction - syn-selectivity - endo mode cyclization - bioactive compound

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