The Journal of Organic Chemistry

Synthesis and stereochemistry of allenes. Part 3. Highly stereoselective synthesis of chiral alkyl allenes by organocopper (I)-induced anti 1, 3-substitution of chiral …

CJ Elsevier, P Vermeer

Index: Elsevier, Cornelis J.; Vermeer, Peter Journal of Organic Chemistry, 1989 , vol. 54, # 15 p. 3726 - 3730

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Abstract

The synthesis of chiral 1, 3-dialkylallenes R1CH= C== CHR2 of high enantiomeric purity, by applying homogeneous reactions between organocopper (1) reagents of the type [(R% uX) MgX-LiX] and chiral propynyl methanesdfonates or sulfinates at low temperatures in THF, is reported. The reactions are generally fasc typically complete conversion is obtained within a few minutes at-60" C. Overall, high anti stereoselectivity is observed. A plausible ...

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