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25.1.11.4 Method 4: Diastereoselective Hydroformylation: Passive Substrate Control

DOI: 10.1055/sos-SD-025-00196

Breit, B.Science of Synthesis, (200725294.

From the mechanism of hydroformylation, it follows that hydrometalation is a syn addition. Since migratory insertion of carbon monoxide into the MC bond occurs with retention of configuration, the overall process is a stereospecific syn addition. Since the hydroformylation of alkenes is an unsymmetric addition reaction, stereogenic centers can be formed either by CH or by CC bond formation, or by both, and in most cases simultaneous control of regiochemistry is required. A new stereogenic center can be formed either by addition to a prochiral alkene (enantiofacial differentiation, see Section 25.1.11.7) or upon addition to a chiral alkene (diastereofacial differentiation and/or kinetic resolution, see Sections 25.1.11.425.1.11.6).

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