Figure 5: Control studies relevant to the synthesis of cyclopentane 15. | Nature Communications

Figure 5: Control studies relevant to the synthesis of cyclopentane 15.

From: Highly stereoselective synthesis of cyclopentanes bearing four stereocentres by a rhodium carbene-initiated domino sequence

Figure 5

(a) Chirality transfer control for the oxy-Cope rearrangement. Matched (b) and mismatched (c) tandem oxy-Cope rearrangement hetero-ene reactions of stereoisomerically pure 3-hydroxy-1,3-hexadienes (13 and epi -13, respectively). Matched (d) and mismatched (e) one-pot cyclopentane (15) syntheses. (f) Justification for high, but imperfect, diastereocontrol during the rhodium-catalysed ylide formation/[2,3]-sigmatropic rearrangement.

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