N-thiophthalimido- arylphenothiazines 2 and triarylamines 3 can be converted to dithiabridged triarylamine hetero[4]helicenes 1 using catalytic amounts of chalcogen substituted Lewis Bases and hexafluoro isopropanol as hydrogen bond donor. The procedure occurs under mild reaction conditions and gives good yields avoiding the use of excesses of Lewis Acids as previously reported. A preliminary study about the possibility to control the M and P absolute stereochemistry of helicenes 1 using enantiopure sulfur containing LBs from the natural chiral pool is also reported.

A Lewis Base Hydrogen Bond Donor (LB/HBD) Organocatalytic Approach to Dithiabridged Triarylamine Hetero[4]helicenes / Lupi M.; Salmi O.; Viglianisi C.; Menichetti S.. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - STAMPA. - 365:(2023), pp. 1705-1712. [10.1002/adsc.202300238]

A Lewis Base Hydrogen Bond Donor (LB/HBD) Organocatalytic Approach to Dithiabridged Triarylamine Hetero[4]helicenes

Lupi M.
Conceptualization
;
Salmi O.
Membro del Collaboration Group
;
Viglianisi C.
Conceptualization
;
Menichetti S.
Project Administration
2023

Abstract

N-thiophthalimido- arylphenothiazines 2 and triarylamines 3 can be converted to dithiabridged triarylamine hetero[4]helicenes 1 using catalytic amounts of chalcogen substituted Lewis Bases and hexafluoro isopropanol as hydrogen bond donor. The procedure occurs under mild reaction conditions and gives good yields avoiding the use of excesses of Lewis Acids as previously reported. A preliminary study about the possibility to control the M and P absolute stereochemistry of helicenes 1 using enantiopure sulfur containing LBs from the natural chiral pool is also reported.
2023
365
1705
1712
Goal 4: Quality education
Lupi M.; Salmi O.; Viglianisi C.; Menichetti S.
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/1314213
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