By Richard C. Larock
This long-awaited, greatly-expanded new version of a best-selling consultant bargains an encyclopedic and systematic selection of priceless artificial technique, together with tens of millions of reactions and artificial variations. the 1st variation has been reviewed within the specialist journals as "clearly...the first selection for researchers looking details on man made transformations." And as "useful to an individual who needs to do natural synthesis, specially these whose concentration isn't really strictly natural chemistry. It offers a...clear street map to the substitute literature and may be stored inside of effortless achieve of the chemist's desk."
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Extra resources for Comprehensive organic transformations: a guide to functional group preparations
Further Reading • For a recent study of squarate ester reactivity see: L. A. Paquette and T. Morwick, 7. Am. Chem. , 1995,117, 1451. • For a review, in German, of the reactions of squaric acid and its derivatives see: A. H. Schmidt, Synthesis, 1980, 961. • For a recent application of this rearrangement to 4-allenylcyclobutanones see: M. Taing and H. W. Moore, J. Org. , 1996, 61, 329. 47 34. The Synthesis of (±)-12a-Deoxytetracycline G. Stork, J. J. La Clair, P. Spargo, R. P. Nargund and N. Totah, J.
Condon, J. Org. , 1993, 55, 1030. 9 Abstracted with permission from J. Org. , 1993,58, 1030 ©1993 American Chemical Society Discussion Points • What is the mechanism of step d? • Give reasons for the use of two equivalents of Lewis acid in step e. • During the ene reaction of step f, a regioisomer of 6 could, in theory, be formed. Propose a structure for this isomer and suggest a reason why its formation was not observed. • Explain the stereoselectivity in steps h and j. • Suggest a possible reason why the phenylselenation reaction of step o required acid catalysis.
When NaH was used as the base in the palladium-catalysed alkylation step a, no enantioselectivity was observed. An enantioselective reaction was obtained with the use of a lithium base or alternatively via the transformation of 2 into its silylated derivative 6. Propose an explanation for this finding. • What is the mechanism of step d? Further Reading • For a review on the selectivity in palladium-catalysed allylic substitutions, see: C. G. Frost, J. Howarth and J. M. J. Williams, Tetrahedron: Asymmetry, 1992, 3, 1089.
Comprehensive organic transformations: a guide to functional group preparations by Richard C. Larock