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The Z -selective cross metathesis of allylic-substituted olefins is explored with recently developed ruthenium-based metathesis catalysts. The reaction proceeds with excellent stereoselectivity for the Z -isomer (typically &gt;95%) and yields of up to 88% for a variety of allylic substituents. This includes the first synthesis of Z -α,β-unsaturated acetals by cross metathesis and their elaboration to Z-α,β-unsaturated aldehydes. In addition, the reaction is tolerant of a variety of cross partners, varying in functionality and steric profile.

Ruthenium-catalysed Z-selective cross metathesis of allylic-substituted olefins