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Bond Cleavage and Product Selectivity

The first step is the nucleophilic ring opening of 7 with organolithiums at low temperature to produce aminophosphine boranes 8. This step occurs regiose-lectively (P-0 bond cleavage) and diastereoselectively (retention of configuration). The selective cleavage of the P-N bond is then performed in methanol with the presence of one equivalent of sulfuric acid. The products are... [Pg.174]

Oxidation of olefins and dienes provides the classic means for syntheses of 1,2- and 1,4-difunctional carbon compounds. The related cleavage of cyclohexene rings to produce 1,6-dioxo compounds has already been discussed in section 1.14. Many regio- and stereoselective oxidations have been developed within the enormously productive field of steroid syntheses. Our examples for regio- and stereoselective C C double bond oxidations as well as the examples for C C double bond cleavages (see p. 87f.) are largely selected from this area. [Pg.123]

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Bond-selectivity

Bonded production

Bonds selection

Cleavage products

Product selection

Selective cleavage

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