Hiyama cross-coupling reaction in the stereospecific synthesis of retinoids.
The first application of the Hiyama reaction to the synthesis of retinoids is reported. A range of organosilicon moieties (siloxanes, silanols and three kinds of "safety-catch" silanols) were successfully coupled, under activation, to obtain trans-retinol or 11-cis-retinol with high yield and stereoselectivity. The advantageous properties of the silicon-based coupling partners and the mild reaction conditions firmly establish the Hiyama reaction as a viable (even superior) alternative to the traditional Suzuki and Stille couplings in the retinoid field.
Montenegro
Javier
J
Departamento de Química Orgánica, Facultade de Química, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain.
Bergueiro
Julián
J
Saá
Carlos
C
López
Susana
S
D015394:Molecular Structure; D012176:Retinoids / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D012176:Retinoids; D012821:Silanes