p K  a  Values of Chiral Brønsted Acid Catalysts: Phosphoric Acids/Amides, Sulfonyl/Sulfuryl Imides, and Perfluorinated TADDOLs (TEFDDOLs) | Zendy

Christ Philipp | Zendy; Lindsay Anita G. | Zendy; Vormittag Sonja S. | Zendy; Neudörfl JörgM. | Zendy; Berkessel Albrecht | Zendy; O'Donoghue AnnMarie C. | Zendy

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p K a Values of Chiral Brønsted Acid Catalysts: Phosphoric Acids/Amides, Sulfonyl/Sulfuryl Imides, and Perfluorinated TADDOLs (TEFDDOLs)

Author(s) -

Christ Philipp,

Lindsay Anita G.,

Vormittag Sonja S.,

Neudörfl JörgM.,

Berkessel Albrecht,

O'Donoghue AnnMarie C.

Publication year - 2011

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201101157

Subject(s) - chemistry , phosphoric acid , sulfonyl , catalysis , brønsted–lowry acid–base theory , organic chemistry , organocatalysis , combinatorial chemistry , stereochemistry , enantioselective synthesis , alkyl

Measure what is measurable , and make measurable what is not so! This timeless quotation by Galileo forms the basis of all quantitative understanding, including asymmetric organocatalysis. We report p K a values for 15 chiral Brønsted acid catalysts in DMSO solutions (see scheme): the strongest acids were bis‐sulfonyl/sulfuryl imides (p K a =1.7–1.9) followed by phosphoric acids/amides (p K a =2.4–4.2). A new class of chiral Brønsted acids, tetrakis‐perfluoroalkyl analogues of TADDOLs (TEFDDOLs) have p K a s from 2.4 to 5.7.

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