Asymmetric synthesis of novel 1,4-aminoalcohol ligands with norbornene and norbornane backbone: use in the asymmetric diethylzinc addition to benzaldehyde

Stereoselective Anhydride Openings

“…During the submission and review period of this article a few new publications related to this topic have appeared. [135][136][137][138][139]…”

“…This review covers the literature until June 2007. During the submission and review period of this article a few new publications related to this topic have appeared. − …”

The role of the C(2) configuration and methyl substitution on the catalytic activity of novel 2,3,3‐ and 2,7,7‐trimethyl‐substituted γ‐aminonorbornan‐2‐ols

“…In contrast, γ‐ and δ‐amino alcohols, where the Zn atom is part of more conformationally‐flexible six‐ or seven‐member chelates, have been much less studied and their catalytic role remains not totally understood 17–28. However, since some γ‐ and δ‐amino alcohols have provided high stereoselectivity levels in the aforementioned reaction,20, 22, 29–31 an increasing interest in the synthesis and application of this kind of chiral ligand has been seen in recent years.…”

Oxamidation of Unsaturated O-Alkyl Hydroxamates: Synthesis of the Madangamine Diazatricylic (ABC Rings) Skeleton

“…Our route to the madangamine core commenced from imide 22 , prepared in high yield by condensation of cis -tetrahydrophthalic anhydride ( 21 ) with allylamine (Scheme ). Treatment of 22 with sodium borohydride in a mixture of i -PrOH–H 2 O (6:1), and reduction of the resulting γ-hydroxy- N- allylamide with LiAlH 4 provided amino alcohol 23 as a single diastereomer in 78% overall yield . Taking advantage of the p- tolylsulfonyl moiety’s duality as N- protecting group and alcohol activator, 23 was treated with excess (3 equiv) p -toluenesulfonyl chloride at low temperature (−30 °C) to generate bis- N,O -tosylate 24 (74% yield) .…”