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Note
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Attempted lactam ring expansion of a precursor possessing β-hydroxyl amide in hand under the standard ACR conditions gave the vinyl-substituted product as a 1.5:1 diastereomeric mixture, possibly via initial elimination of the labile alkoxy group and subsequent vinylogous amide enolate induced ACR.
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25
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77951784532
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For a mechanism on the 2-alkyl-3-oxo-amide reduction with borohydride species
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For a mechanism on the 2-alkyl-3-oxo-amide reduction with borohydride species
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29
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77951820451
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Note
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2 synthesized from the 14-membered macrolactam possessing the (R)-configuration at the stereogenic center of interest (see the Supporting Information).
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