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- Title
The Role of Aromatic Alcohol Additives on Asymmetric Organocatalysis Reactions: Insights from Theory.
- Authors
Banerjee, Subhrashis; Vanka, Kumar
- Abstract
The presence of an aromatic additive has been seen to enhance, often significantly, the enantioselectivity and yield in asymmetric organocatalysis. Considering their success across a dizzying range of organocatalysts and organic transformations, it would seem unlikely that a common principle exists for their functioning. However, the current investigations with DFT suggest a general principle: the phenolic additive sandwiches itself, through hydrogen bonding and π⋅⋅⋅π stacking, between the organocatalyst coordinated electrophile and nucleophile. This is seen for a wide range of experimentally reported systems. That such complex formation leads to enhanced stereoselectivity is then demonstrated for two cases: the cinchona alkaloid complex (BzCPD), catalysing thiocyanation (2‐naphthol additive employed), as well as for L‐pipecolicacid catalysing the asymmetric nitroaldol reaction with a range of nitro‐substituted phenol additives. These findings, indicating that dual catalysis takes place when phenolic additives are employed, are likely to have a significant impact on the field of asymmetric organocatalysis.
- Subjects
ORGANOCATALYSIS; CINCHONA alkaloids; ELECTROPHILES; ADDITIVES; HYDROGEN bonding; NITROALDOL reactions
- Publication
Chemistry - An Asian Journal, 2024, Vol 19, Issue 4, p1
- ISSN
1861-4728
- Publication type
Article
- DOI
10.1002/asia.202300997