Tetrahedron p. 2831 - 2846 (1986)
Update date:2022-07-29
Topics:
Funk, Raymond L.
Abelman, Matthew, M.
Munger, John D.
Macrocyclic ketene acetals 3 undergo Claisen rearrangements smoothly and constitute a viable and general approach to hetero- or carbocyclic ring systems 4.This novel ring contraction process is subject to high internal asymmetric induction (cf. lactones 7 -> carbocycles 8) as well as relative asymmetric induction in the rearrangements of ketene acetals derived from lactones 18, 23 and 27.Finally, N-benzoylmeroquinene methyl ester (37) was prepared to demonstrate the potential of this methodology in heterocycle synthesis.
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Doi:10.1016/S0040-4039(00)84451-2
(1986)Doi:10.1039/c3ra43989e
(2013)Doi:10.1016/j.bmc.2008.04.023
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(2008)Doi:10.1021/ja711447s
(2008)
