Applications of both halogen and chalcogen bonding in organocatalysis are by now well established with various examples. However, the combination of both interactions within one catalyst is currently unknown. Herein, we describe the synthesis of such a mixed chalcogen‐ and halogen‐bond donor and present a first indication of its catalytic activity in a benchmark reaction.
Oxa-Diels-Alder reaction is a straightforward, atom-economical process for the construction of six membered oxa-cycle which is a privileged structure due to its omnipresence in several pharmaceuticals and natural products. Like many other asymmetric transformations, organocatalysis provides an elegant pathway to their synthesis via [4+2] annulation under mild reaction conditions. The oxa-Diels reactions either utilize α,β-unsaturated carbonyl as oxadiene with a suitable dienophile or simple carbonyl as dienophile with other dienes. A range of organocatalysts have been explored in the past decade to execute this strategy. The catalysts induce stereoselectivities via two basic reactivities: 1) Formation of chiral intermediates, 2) Selectively activating suitable reactants in transition state. The present review assembles organocatalyzed asymmetric oxa-Diels-Alder reactions published in last ten years’ time span with detailed discussion on mechanistic approaches.
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