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Highly Enantioselective Organocatalytic Conjugate Addition of Malonates to Acyclic α,β-Unsaturated Enones

✍ Scribed by Nis Halland; Pompiliu S. Aburel; Karl Anker Jørgensen

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
159 KB
Volume
115
Category
Article
ISSN
0044-8249

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Highly Enantioselective Organocatalytic
Highly Enantioselective Organocatalytic Conjugate Addition of Malonates toAcyclic α,β-Unsaturated Enones
✍ Nis Halland; Pompiliu S. Aburel; Karl Anker Jørgensen 📂 Article 📅 2003 🏛 John Wiley and Sons 🌐 English ⚖ 159 KB

Even though the first reports of enantioselective organocatalysis by Wiechert et al. and Hajos and Parrish appeared almost three decades ago, [1] the field of asymmetric catalysis has been dominated by metal catalysis. It is only recently that asymmetric organocatalysis has received renewed attentio

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## Abstract The first example of an organocatalytic asymmetric Michael addition of aldehydes to α,β‐unsaturated thiol esters promoted by chiral diphenylprolinol silyl ether is presented. The reaction occurs with good yields, diastereoselectivity and excellent enantioselectivity.

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Organocatalysis [1] has expanded widely within the last few years, since the rediscovery of the proline-catalyzed aldol reaction. [2] Since then, several different methods, such as fluorination, [3] chlorination, [4] bromination, [5] sulfenylation, [6] amination, [7] and Mannich reactions, [8] have