Chiral 2-arylpropyl-2-sulfinamide and chiral n-2-arylpropyl-2-sulfinylimines and synthesis thereof
AssigneesTexas Tech University, Nanjing University, Institute of Chemistry and Biomedical Sciences
InventorGuigen LI
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Abstract
Provided herein are novel chiral sulfinamide and imine compounds. Also provided herein are methods of synthesizing novel chiral sulfinamide and imine compounds comprising simplified purification methods when compared to prior methods. The novel chiral sulfinamide and imine compounds are useful, for example, in the synthesis of complex natural products and pharmaceutical important compounds.
Claims19
A compound according to Formula 1001a or 1001b:
- wherein:
- Y is amino or imino;
- and
- RA is lower alkyl or aryl.
A method for preparing a compound of Formula Ia or Ib,
- wherein the compound of Formula Ia is formed by:
- a. reacting a compound of formula i2 in the presence of a compound of formula i3a to form a compound of formula i4a:
- b. reacting the compound of formula i4a in the presence of TBDMS-NH2 to form a compound of formula i5a:
- and
- c. reacting the compound of formula i5a in the presence of TBAF to form the compound of formula Ia:
- and
- wherein the compound of Formula Ib is formed by:
- a. reacting a compound of formula i2 in the presence of a compound of formula i3b to form a compound of formula i4b:
- b. reacting the compound of formula i4b in the presence of TBDMS-NH2 to form a compound of formula i5b:
- and
- c. reacting the compound of formula i5b in the presence of TBAF to form the compound of formula Ib:
- wherein each R1 is independently hydrogen, alkyl or aryl.
A method for the preparation of a compound of formula 1002a or 1002b (1002 (a, b)), formula IIIa, or IIIb,
- wherein:
- the compound of formula 1002 (a, b) is formed by reacting a compound of formula 1003a or 1003b (1003 (a, b)) with a compound of formula i6 to form a compound of formula 1002 (a, b):
- the compound of formula IIIa is formed by reacting a compound of formula Ia with a compound of formula i6 to form a compound of formula IIIa:
- the compound of formula IIIb is formed by reacting a compound of formula Ib with a compound of formula i6 to form a compound of formula IIIb:
- and
- wherein each of R1, R2, and R3 is independently hydrogen, alkyl or aryl.
Dependencies are inferred from the claim text.