Asymmetric Pauson-Khand Cyclizations of 1-Sulfinylenynes

Abstract

The use of sulfoxides as chiral auxiliaries in intramolecular Pauson-Khand (PK) reactions is described. In particular, the tert-butylsulfinyl group acts as a very efficient chiral auxiliary in intramolecular PK reactions of 1-sulfinyl-1,6-enynes. As the starting enynes are readily available in optically pure form and the final desulfinylation step is high yielding, this procedure constitutes an efficient alternative to the synthesis of enantiomerically pure bicyclo[3.3.0]oct-1-en-3-ones.

Key words

sulfoxides - Pauson-Khand reaction - asymmetric synthesis - enynes - bicyclo[3.3.0]octenones

References

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9

The o-(N,N-dimethylamino)phenylsulfinyl group has been used as an efficient chiral auxiliary in asymmetric Heck reactions, see ref. [5] .

10

The crystallographic data of compound 4cA have been deposited at the Cambridge Crystallographic Data Centre (supplementary publication nº CCDC 133957); see also ref. [7] .