A new chiral benzimidazole‐pyrrolidine has been devised, which exhibits excellent activities in aminocatalyzed aldol reactions, leading to aldol products in high yields and enantioselectivities in the presence of an equimolar amount of a Brönsted acid. This organocatalyst has demonstrated remarkable reactivities in aldol processes even with equimolar amounts of aldehyde and ketone in THF. A discussion of the role of the Brönsted acid as a co‐catalyst is provided along with some applications of this new class of organocatalyst in Robinson annelation and α‐amination processes. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

Little is known about the ability of α-linolenic acid (Ln) to remain in the sn-2 position of TG during the absorption process. The goal of this study was to determine the Ln distribution in the lymph (Study 1) and plasma (Study 2) TG of rats fed a single i.g. load of structured TG [300 mg/rat of either oleic acid (O)/Ln/O TG (OLnO) or Ln/O/O TG (LnOO), n = 7 rats]. In an early fraction (3-4 h) of lymph (OLnO group; 100% Ln in the sn-2 position), 46 ± 2% Ln was maintained in this position in lymph TG. There was even less (29 ± 6%) in the last fraction (7-24 h) (P < 0.05). Ln was also found (9 ± 3%) in the sn-2 position of lymph TG in the LnOO group. The Ln content in lymph phospholipids was twice as high in rats when they were fed LnOO (4.2 ± 0.1%) than OLnO (2.3 ± 0.2%) (P < 0.005). Six hours postprandially (Study 2), 21 ± 3% of the Ln incorporated into plasma TG was located in the sn-2 position in the OLnO group compared to 13 ± 2% in the LnOO group (P < 0.001). Overall, these results indicate that the amount of Ln that moved from the sn-2 position of structured TG to the sn-1(3) position of lymph TG increased during absorption. This may account for a substantial hydrolysis of the 2-monolinolenylglycerols in enterocytes, leading to the intramolecular redistribution of Ln in lymph TG and, consequently, in plasma TG.

The new chiral BIP catalyst exhibits excellent activities in amino-catalyzed aldol reactions when combined with an equimolar amount of a Broensted acid. The system is also examined in Robinson anellation and α-amination processes. -(LACOSTE, E.; VAIQUE, E.; BERLANDE, M.; PIANET, I.; VINCENT* JEAN-MARC; LANDAIS, Y.; Eur.