Diastereodivergent Henry Reaction for the Stereoselective Construction of Nitrogen‐Containing Tetrasubstituted Carbons: Application to Total Synthesis of Manzacidins A and C
β,β‐Disubstituted β‐amino alcohols has been synthesized in a diastereodivergent manner from chiral secondary nitroalkanes as starting materials. In this key Henry reaction, the use of different protecting groups resulted in the diastereoselective construction of the tetrasubstituted carbon stereocen...
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Veröffentlicht in: | Asian journal of organic chemistry 2017-12, Vol.6 (12), p.1760-1763 |
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Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | β,β‐Disubstituted β‐amino alcohols has been synthesized in a diastereodivergent manner from chiral secondary nitroalkanes as starting materials. In this key Henry reaction, the use of different protecting groups resulted in the diastereoselective construction of the tetrasubstituted carbon stereocenter with different configuration. Based on this methodology, a total synthesis of manzacidins A and C has been achieved.
Henry reaction of chiral secondary nitroalkanes constructed nitrogen‐containing tetrasubstited carbon stereocenters with high diastereoselectivity. Protecting groups of the nitroalkanes played a key role to control the diastereoselectivity. Using the Henry adducts as key intermediates, a total synthesis of manzacidins A and C has been achieved. |
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ISSN: | 2193-5807 2193-5815 |
DOI: | 10.1002/ajoc.201700568 |