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- Title
Formal Aminocyanation of α,β-Unsaturated Cyclic Enones for the Efficient Synthesis of α-Amino Ketones.
- Authors
Sun, Chunrui; O'Connor, Matthew J.; Lee, Daesung; Wink, Donald J.; Milligan, Robert D.
- Abstract
Installation of amino functionality on organic molecules through direct CN bond formation is an important research objective. To achieve this goal, a 1,2-aminocyanation reaction was developed. The reaction occurs through the formation of pyrazolines by means of a formal dipolar cycloaddition of cyclic α,β-unsaturated ketones with lithium trimethylsilyldiazomethane followed by novel protonolytic NN bond cleavage under mild conditions. This two-step process provides a diverse array of structurally complex free and mono-alkylated α-amino ketones in excellent yields.
- Subjects
AMINO compounds; CARBONYL compounds; KETONE synthesis; LITHIUM compounds; RING formation (Chemistry)
- Publication
Angewandte Chemie International Edition, 2014, Vol 53, Issue 12, p3197
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201309435