Categories: C-C Bond Formation > Oxygen-containing molecules > Carbonyl compounds >
Synthesis of β-hydroxy ketones and aldehydes (using Umpolung)
| Related:
|
 |
Name Reactions
Recent Literature
A N-heterocyclic carbene catalyzed the synthesis of aldol products in good
yields involving carbonyl umpolung of enals to form nucleophiles, which attack
electrophilic terminal epoxides, regioselectively. These aldols have been used
in a facile and highly cis-selective synthesis of tetrahydropyran-4-ones.
L. D. S. Yadav, S. Singh, V. K. Rai, Synlett, 2010,
240-246.
A linchpin coupling protocol is based on anion relay chemistry (ARC). The
addition of an anion to an epoxide, bearing on a distal carbon a trialkyl silyl
group and an anion stabilizing group furnishes upon epoxide ring opening an
oxyanion. Addition of HMPA triggers a solvent controlled 1,4-Brook rearrangement
leading to a new distal anion, which reacts with various electrophiles.
A. B. Smtih, III, M. Xiang, J. Am. Chem. Soc., 2006,
128, 66-67.
