Molybdenum-mediated diastereoselective synthesis of 2-heterobicyclo[4.4.0]decene derivatives

Ming Chang P. Yeh; Chong Nan Chaung

doi:10.1039/p19960002167

Molybdenum-mediated diastereoselective synthesis of 2-heterobicyclo[4.4.0]decene derivatives

Ming Chang P. Yeh^*
, Chong Nan Chaung

^*Corresponding author for this work

Department of Chemistry

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

10 Citations (Scopus)

Abstract

The addition of a variety of functionalized zinc-copper reagents RCu(CN)ZnI 2 to (η⁵-cyclopentadienyl)(η ⁴-cyclohexa-1,3-diene)dicarbonylmolybdenum cation 1 proceeds in a highly regio- and stereo-specific fashion to generate (η⁵-cyclopentadienyl)(π-allyl)dicarbonylmolybdenum complexes 3 with a functionalized side-chain at the C-4 position of the ring. Intramolecular cyclization of the (π-allyl)molybdenum complexes containing a pendant alcohol, carboxylic acid, thiol or amine functionality affords fused 2-heterobicyclo[4.4.0]decene derivatives.

Original language	English
Pages (from-to)	2167-2172
Number of pages	6
Journal	Journal of the Chemical Society - Perkin Transactions 1
Issue number	17
DOIs	https://doi.org/10.1039/p19960002167
Publication status	Published - 1996 Sept 7

ASJC Scopus subject areas

General Chemistry

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title = "Molybdenum-mediated diastereoselective synthesis of 2-heterobicyclo[4.4.0]decene derivatives",

abstract = "The addition of a variety of functionalized zinc-copper reagents RCu(CN)ZnI 2 to (η5-cyclopentadienyl)(η 4-cyclohexa-1,3-diene)dicarbonylmolybdenum cation 1 proceeds in a highly regio- and stereo-specific fashion to generate (η5-cyclopentadienyl)(π-allyl)dicarbonylmolybdenum complexes 3 with a functionalized side-chain at the C-4 position of the ring. Intramolecular cyclization of the (π-allyl)molybdenum complexes containing a pendant alcohol, carboxylic acid, thiol or amine functionality affords fused 2-heterobicyclo[4.4.0]decene derivatives.",

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N2 - The addition of a variety of functionalized zinc-copper reagents RCu(CN)ZnI 2 to (η5-cyclopentadienyl)(η 4-cyclohexa-1,3-diene)dicarbonylmolybdenum cation 1 proceeds in a highly regio- and stereo-specific fashion to generate (η5-cyclopentadienyl)(π-allyl)dicarbonylmolybdenum complexes 3 with a functionalized side-chain at the C-4 position of the ring. Intramolecular cyclization of the (π-allyl)molybdenum complexes containing a pendant alcohol, carboxylic acid, thiol or amine functionality affords fused 2-heterobicyclo[4.4.0]decene derivatives.

AB - The addition of a variety of functionalized zinc-copper reagents RCu(CN)ZnI 2 to (η5-cyclopentadienyl)(η 4-cyclohexa-1,3-diene)dicarbonylmolybdenum cation 1 proceeds in a highly regio- and stereo-specific fashion to generate (η5-cyclopentadienyl)(π-allyl)dicarbonylmolybdenum complexes 3 with a functionalized side-chain at the C-4 position of the ring. Intramolecular cyclization of the (π-allyl)molybdenum complexes containing a pendant alcohol, carboxylic acid, thiol or amine functionality affords fused 2-heterobicyclo[4.4.0]decene derivatives.

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Molybdenum-mediated diastereoselective synthesis of 2-heterobicyclo[4.4.0]decene derivatives

Abstract

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