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Strong Organic Bases
No.150(December 2012)
MTBD (1) and TBD (2) are bicyclic guanidine organic bases. The pKa values of the conjugate acids of these bases in acetonitrile are 25 and 26, respectively.1) 1 and 2 show relatively strong basicities comparing to DBU and TMG (tetramethylguanidine), which are well known as organic bases.
1. Selective Deprotonation of Sulfonamide2a)
2. Aziridine Ring-Opening Reaction2b)
Instead of DBU and CuOAc, the use of 2 as a base gives better yields (59% to 78%).
Instead of DBU and CuOAc, the use of 2 as a base gives better yields (59% to 78%).
3. Wittig, Horner–Emmons Reactions3)
In many cases, the reactions are carried out without anhydrous and inert conditions.
In many cases, the reactions are carried out without anhydrous and inert conditions.
References
- 1)Basicity scale in acetonitrile
- 2)Total synthesis of Ustiloxin D
- 3)Wittig and Horner–Emmons reactions
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