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US 12,492,217 B2Granted
Reagents and their use for modular enantiodivergent synthesis of C—P bonds
AssigneesBristol-Myers Squibb Company, The Scripps Research Institute
InventorsDongmin Xu, Nazaret Rivas-Bascón, Kyle W. Knouse, Natalia M. Padial, Bin Zheng, Julien C. Vantourout, Michael Anthony Schmidt, Martin D. Eastgate, Phil S. Baran
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Abstract
The disclosure describes chiral P(V)-based reagents and their uses for the modular, scalable, and stereospecific synthesis of chiral phosphines, phosphine oxides and particular oligonucleotides.
Claims19
A compound of Formula (I):
- or a salt thereof, wherein:
- R1 is C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-10 aryl, or C-attached heteroaryl, wherein R1 is optionally substituted with one or more, the same or different, Ra groups;
- Ra is deuterium, CD3, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, halogen, CF3, C1-6 alkoxy, C3-10 cycloalkyl, C6-10 aryl or C-attached heteroaryl;
- R4 is hydrogen, C1-6 alkyl, C2-6 alkenyl, or C2-6 alkynyl;
- R5 is C1-6 alkyl, C2-6 alkenyl, or C2-6 alkynyl;
- R7 is a substituent that substitutes for a hydrogen and is one of C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, or C6-10 aryl;
- and
- n is 0, 1, 2, 3, 4, 5, 6, 7, or 8.
5 more elements
A method of making a thiophosphinic acid, the method comprising:
- reacting a carbanion reagent with a compound of Formula (Ia):
- a salt thereof, an enantiomer thereof, or a combination thereof;
- wherein
- R1 is C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-10 aryl, or C-attached heteroaryl, wherein R1 is optionally substituted with one or more, the same or different, Ra groups;
- Ra is deuterium, CD3, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, halogen, CF3, C1-6 alkoxy, C3-10 cycloalkyl, C6-10 aryl or C-attached heteroaryl;
- to form a thiophosphinic acid.
3 more elements
Dependencies are inferred from the claim text.