Towards Tartaric-Acid-Derived Asymmetric Organocatalysts

Towards Tartaric-Acid-Derived Asymmetric Organocatalysts

Tartaric acid is one of the most prominent naturally occurring chiral compounds. Whereas its application in the production of chiral ligands for metal-catalysed reactions has been exhaustively investigated, its potential to provide new organocatalysts has been less extensively explored. Nevertheless, some impressive results, such as the use of TADDOLs as chiral H-bonding catalysts or of tartrat...

Syntheses of C2-symmetric vicinal diamines derived from tartaric acid

C2-symmetric vicinal diamines 3b–f, derived from L-tartaric acid, with increasingly bulky terminal ether functionalities were prepared using two distinct sequences. Diamines 3b,c were obtained from the corresponding vicinal diols 4b,c, while diamines 3d–f were generated from dihydroxydiazide 7 via deprotection–reprotection strategies. © 1999 Elsevier Science Ltd. All rights reserved.

Asymmetric catalytic cycloetherification mediated by bifunctional organocatalysts.

Oxacyclic structures such as tetrahydrofuran (THF) rings are commonly found in many bioactive compounds, and this has led to several efforts toward their stereoselective syntheses. However, the process of catalytic asymmetric cycloetherification for their straightforward synthesis has remained a challenge. In this study, we demonstrate a novel asymmetric synthesis method for THF via the catalyt...

Camphor-derived C1-symmetric chiral diamine organocatalysts for asymmetric Michael addition of nitroalkanes to enones.

A series of stable C(1)-symmetric chiral diamines (2a–2l) were conveniently synthesized by condensing exo-(-)-bornylamine or (+)-(1S,2S,5R)-menthylamine with various commercially available Cbz-protected amino acids. Among them, 2a can efficiently promote the Michael addition of nitroalkanes to a broad scope of enones with high yields (up to 96%) and excellent enantioselectivities (up to 98%) un...

Significance of urinary tartaric acid.