Nucleophilic Addition Reactions of 1,4-Diketones Derived from Tartaric Acid: Synthesis of TADDOL Analogues

Abstract

A systematic investigation of the reduction and Grignard reagents addition to 1,4-diketones derived from tartaric acid was carried out. It was found that the reduction proceeded with high selectivity using K-Selectride as the reducing agent; while Grignard reagent addition was highly dependent on structure of the dione as well as on the Grignard reagent. The resultant 1,4-diols represent a series of novel TADDOL analogues.

Key words

asymmetric synthesis - TADDOL - stereoselective addition

References

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8

The low selectivity (dr 4a:5a = 67:33) observed in the reduction of diketone 3a with L-Selectride can be explained by the chelation of lithium ion which has a propensity to chelate to a greater extent.