Stereocontrol in organic synthesis using silicon-containing compounds. A synthesis of methyl (+)-nonactate

M Ahmar, C Duyck, I Fleming

Index: Ahmar, Mohammed; Duyck, Catherine; Fleming, Ian Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 17 p. 2721 - 2732

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Abstract

(3Z, 2S)-7, 7-Ethylenedioxyhex-3-en-2-yl N-phenylcarbamate 7 gave the allylsilane 8,(2E, 4S)-7, 7-ethylenedioxy-4-dimethyl (phenyl) silylhept-2-ene, introducing one stereogenic centre carrying a silyl group. Hydroboration–oxidation gave (2S, 4S)-7, 7-ethylenedioxy-4- dimethyl (phenyl) silylheptan-2-ol 9, controlling a second stereogenic centre. Conjugate addition of the phenyldimethylsilylcuprate reagent to the α, β-unsaturated imide (2′ E, 6 ...