Studies on Aldol Reactions of Nortropinone Derivatives in Solution and on Solid Phase

(1RS,2SR,5SR)-9-Benzyl-2-[(1RS)-1-hydroxybenzyl]-9-azabicyclo[3.3.1]nonan-3-one from synchrotron data

“…For recent background literature on the synthesis, structure and applications of related granatane-derived aldols, see: Lazny et al (2011a) and references cited therein. For the stereoselective syntheses, applications and structures of related tropinone aldols, see: Sienkiewicz et al (2009); Lazny et al (2011b); Brzezinski et al (2012) and for related nortropinone aldols, see: Lazny et al (2001Lazny et al ( , 2010; Lazny & Nodzewska (2003).…”

Determination of the N-invertomer stereochemistry in N-substituted nortropanones and norgranatanones using computational and NMR methods

“…However, as far as we know, there has been no experimental or computational study concerning the distribution of the higher N-alkyl or N-aryl invertomers in tropanes or granatanes in water (or even other polar solvents), which are essential for biological systems and green synthetic reactions. The enantioselectivity of deprotonation and diastereoselectivity of aldol reactions of higher N-alkyl homologues of tropinone [21,42,43] and granatanone [34] is affected by the configurational preference of the N-substituents in reaction medium. In an effort to extend the aqueous aldol reactions [44] to higher N-alkyl substrates, we decided to examine their Ninvertomer preferences.…”

An Investigation of the Enolization and Isomeric Products Distribution in the Water Promoted Aldol Reaction of Tropinone and Granatanone

“…Before our preliminary communication on aldol addition of tropinone and granatanone (pseudopelletierine, 2, 9-methyl-9-azabicyclo[3.3.1]nonan-3-one) to aldehydes (Scheme 1) in the presence of water [17], the only method for accessing these exo,anti-aldols [18,19] or related nor-analogues [20,21] was reactions promoted by lithium amide bases under anhydrous conditions. Moreover, our solventless reaction in the presence of small (ca.…”