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. 2013 Sep 6;15(17):4462-5.
doi: 10.1021/ol4019985. Epub 2013 Aug 22.

Stereocontrolled synthesis of (E,Z)-dienals via tandem Rh(I)-catalyzed rearrangement of propargyl vinyl ethers

Dinesh V Vidhani  1 , Marie E Krafft, Igor V Alabugin
Affiliations

Stereocontrolled synthesis of (E,Z)-dienals via tandem Rh(I)-catalyzed rearrangement of propargyl vinyl ethers

Dinesh V Vidhani et al. Org Lett. .

Abstract

A novel Rh(I)-catalyzed approach to functionalized (E,Z) dienals has been developed via tandem transformation where a stereoselective hydrogen transfer follows a propargyl Claisen rearrangement. Z-Stereochemistry of the first double bond suggests the involvement of a six-membered cyclic intermediate whereas the E-stereochemistry of the second double bond stems from the subsequent protodemetalation step giving an (E,Z)-dienal.

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