Assymetryc catalisys in organic chemistry by Noyori R

By Noyori R

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Rings within chains) into molecular segments is frequently best accomplished by acyclic bond disconnection, especially when such rings are separated by one or more chain members. e. exo) to a ring, or 1, 2, or 3 bonds removed from it, depending on the type of ring which is involved. 6. Skeletal bonds directly to remote stereocenters or to stereocenters removed from functional groups by several atoms are preserved. Those between non-stereocenters or double bonds which lie on a path between stereocenters are strategic for disconnection, especially if that path has more than two members.

In a structure with several isolated rings embedded within the main skeleton, the most strategic ring for disconnection topologically will be the most centrally located, especially if it is a size which allows two-bond disconnection (usually 3-, 4- or 6membered rings). 5 Disconnection of Fused-Ring Systems Strategic considerations based on topological analysis of cyclic structures become more significant as the numbers of rings and interconnections between such rings increase. Polycyclic structures in which two or more rings are fused together have long occupied an important place in synthesis, since they are common and widely distributed in nature, especially for 5- and 6-membered rings.

It is this fact which lent priority to examining the disconnection pathway via 39 over the other 5 alternatives. Of those remaining alternatives the disconnection of a-b and e-f bonds of 37 is signaled by the fact that centers a and f are carbon-bearing stereocenters which potentially can be set in place with complete predictability because of the strict suprafacial (cis) addition course of the Diels-Alder process with regard to the dienophile component. This disconnection requires the introduction of a π-bond between the carbons corresponding to c and d in 37.

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