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44
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Whereas employing methyl lithium in lieu of Grignard reagents yields a mixture of both diastereomers. We assume that the complexation of the aldehyde, apart from steric factors and its spatial fixation is crucial for the excellent stereoselectivity. The configuration of the newly generated stereocenter was assigned by transformation of compound 10 into a dioxydecaline derivative and comparison of the chemical shifts to literature data; see: K. Pihlaja, J. Mattinen and J. Czombos, J. Prakt. Chem./ Chem.-Ztg.. 1997, 339, 77-78.
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51
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20844442543
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-
note
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Depending on reaction time, conditions and number of equivalents of ylide, the major side products were either the a,β-unsaturated ketone or the cyclopropylated consecutive product.
-
-
-
-
52
-
-
20844443552
-
-
note
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The relative configuration of both epoxides was assigned by NOE.
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