Organocatalytic asymmetric transformations of modified Morita-Baylis-Hillman adducts
Chiral Lewis basic tertiary amines or phosphines can enable properly modified Morita-Baylis-Hillman (MBH) adducts to undergo asymmetric allylic substitutions with a wide range of nucleophiles. In addition, assisted by a Brønsted base, chiral Lewis bases can also catalytically convert modified MBH ad...
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Veröffentlicht in: | Chemical Society reviews 2012-01, Vol.41 (11), p.411-4112 |
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Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | Chiral Lewis basic tertiary amines or phosphines can enable properly modified Morita-Baylis-Hillman (MBH) adducts to undergo asymmetric allylic substitutions with a wide range of nucleophiles. In addition, assisted by a Brønsted base, chiral Lewis bases can also catalytically convert modified MBH adducts into allylic ylides, which can be engaged in a variety of asymmetric annulation reactions. This
tutorial review
will focus on such chiral Lewis base-catalysed asymmetric transformations of MBH adducts, especially those developed over the past five years, allowing for the rapid construction of densely functionalised chiral molecules with high levels of regio- and stereoselectivities.
This tutorial review summarises the asymmetric allylic alkylations or [3 + 2] annulations with racemic modified Morita-Baylis-Hillman adducts by the catalysis of chiral Lewis basic amines or phosphines. |
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ISSN: | 0306-0012 1460-4744 |
DOI: | 10.1039/c2cs35017c |