By Alfred Hassner
Enantioselective artificial equipment usually are not merely within the leading edge of chemical and pharmaceutical learn yet job during this sector is continually expanding. it's motivated by means of the urgency to procure medicinal drugs or compounds of medicinal curiosity as unmarried anantiomers, and the keeness to synthesize typical items in nonracemic shape. This quantity provides seven chapters from pioneers and gurus during this speedily increasing box.
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Extra resources for Advances in Asymmetric Synthesis, Volume 3, Volume 3 (Advances in Asymmetric Synthesis)
Enantioselective Deprotonation of Cyclic Ketones 47 Figure 5. Ball and stick model of the most stable conformer of tropinone. ^^ Although the stereoelectronic preference is difficult to measure and could be small, the P-face of tropinone should also be much more exposed to an attack by the base for steric reasons (Figure 5)—the notion that the P-face is less sterically hindered was confirmed later by results of electrophilic attack on tropinone enolate (vide infra). Before addressing the enantioselective deprotonation the fundamentals of the tropinone lithium enolate chemistry had to be established, since little was known about generation of tropinone enolate under kinetic conditions.
36. ; Winkler, J. ; Saccomano, N. A. Tetrahedron Lett. 1983,24,465. 37. ; Nelson, D. Tetrahedron Lett. 1965, 3376 and references cited therein. 38. ; Euatace, E. J. / Org. ; d'Angelo, J. Tetrahedron Lett. 1976,6087. 36 YOSHINORI YAMAMOTO, NAOKI ASAO, and NAOFUMI TSUKADA 39. Review articles: Paquette, L. A. In Asymmetric Synthesis', Morison, /. ; Academic Press: New York. 1984, Vol. 3, PartB, Chap. Angew. Chem. , Ed Engl. 1984,23,876. 40. ; Uyehara, T; Yamamoto, Y J. Org. Chem. 1992,57, 5049. 41.
The predominant formation of the anti-isomer 105 can be explained by a modified Felkin-Anh model 107 in which the largest silyloxymethyl group is in the anti position and the medium methyl group is in the inside and the lithium amide reagents attack the P-carbon of 104a from the less hindered outside. )-93 to 104a produced the i>'n-diastereoisomer 108 with essentially 100% de in 84% yield (Eq. 25). On the other hand, the addition of (5)-93 to 104a gave the an/i-diastereoisomer 109 with essentially 100% de in 95% yield (Eq.
Advances in Asymmetric Synthesis, Volume 3, Volume 3 (Advances in Asymmetric Synthesis) by Alfred Hassner