Iridoids : enantioselective synthesis of loganin via an asymmetric diels-alder reaction

Essential oils-oriented chiral esters as potential pesticides: Asymmetric syntheses, characterization and bio-evaluation

“…The important chiral intermediates 1 were obtained by highly diastereoselectivity conjugate addition of Grignard reagents to Nenoylsultams (Vandewalle et al, 1986) according to the modified methods (Cao et al, 2008(Cao et al, , 2009). Hydrolysis of adducts 1 under mild conditions provided the chiral acids 2.…”

Amphidinolide B: Total Synthesis, Structural Investigation, and Biological Evaluation

“…TMSCl (3.96 g, 4.5 mL, 36.5 mmol) was then added followed by a solution of known sultam 59 56 (6.9 g, 24.3 mmol) in THF (60 mL). After another 90 min, the reaction was quenched with NH 4 Cl-NH 4 OH (9:1, pH 9, 60 mL), warmed to rt.…”

Recent advances in the application of the Oppolzer camphorsultam as a chiral auxiliary

“…These compounds can be transformed into chiral ketones, alcohols, aldehydes, and carboxylic acids, which are significant and valuable intermediates for the total synthesis of natural and medicinal products. The asymmetric conjugate addition of Grignard reagents to N-enoylsultam 63 which is generated via acylation of the camphorsultam with acyl chlorides 50 Under optimized conditions, the asymmetric conjugate addition of Grignard reagents to N-enoylsultam 63 afforded the 1,4-addition product 64 in excellent regioselectivities (>20:1) and with good to excellent diastereoselectivities. Compound 64 was then reduced upon treatment with NaBH 4 to provide the desired compound 66.…”