MSTFA as an Effective TMS Source for the TMSOTf-Catalzyed Synthesis of Cyclic Acetals.
J Org Chem
; 89(8): 5555-5559, 2024 Apr 19.
Article
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| MEDLINE
| ID: mdl-38592064
ABSTRACT
Commercially and readily available MSTFA [2,2,2-trifluoro-N-methyl-N-(trimethylsilyl)acetamide] was identified as a highly effective TMS (trimethylsilyl) source for the convenient preparation of cyclic acetals under modified Noyori's conditions. The reactions proceeded smoothly under mild conditions, affording a wide range of the corresponding cyclic acetals with excellent yields in the presence of catalytic TMSOTf (trimethylsilyl trifluoromethanesulfonate). The present method does not require a large excess of diols that can be valuable and does not require presynthesized silylated diols. In contrast to other silylating reagents such as BSA [N,O-bis(trimethylsilyl)acetamide] and BSTFA [N,O-bis(trimethylsilyl)trifluoroacetamide], the application of MSTFA avoided the inhibition of catalytic acetalization by the side product 2,2,2-trifluoro-N-methylacetamide.
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Idioma:
En
Revista:
J Org Chem
/
J. org. chem
/
Journal of organic chemistry
Año:
2024
Tipo del documento:
Article
País de afiliación:
Estados Unidos