Abstract
The full scope and limitations of solution and solid phase one-pot three component N- acyliminium ion reactions are detailed. After studying the scope in solution with respect to the carbamate, nucleophile and aldehyde component, a 'translation' was made to the solid phase. The solid phase reactions were eventually carried out using the so-called SEC linker system, which was previously developed in our group. In order to maximize the scope of the nucleophile component, additional studies were successfully conducted using two-step processes involving stable N-acyliminium ion precursors.
Highlights
Numerous types of reactions have been ‘translated’ from the solution to the solid phase, so that solid phase combinatorial chemistry may currently enable the synthesis of various compound libraries of any size
In a series of publications, it was shown by our group2,3,4,5 and by others6 that N-acyliminium ion chemistry can be efficiently carried out on a solid phase, provided that an appropriate linker system is used
In conjunction with a preliminary publication on one-pot three component N-acyliminium ion reaction for the synthesis of homoallylic amines,2 this paper will detail a full account of the scope and limitations of this reaction
Summary
Numerous types of reactions have been ‘translated’ from the solution to the solid phase, so that solid phase combinatorial chemistry may currently enable the synthesis of various compound libraries of any size.1 solid phase reactions should not deliver as many compounds as possible, but rather as ‘diverse’ compounds as possible. Allyl carbamate 11 (100 mg, 0.99 mmol), benzaldehyde (101 μL, 0.99 mmol) allyltrimethylsilane (157 μL, 0.99 mmol) and BF3⋅OEt2 (125 μL, 0.99 mmol) in CH2Cl2 (2 mL) were reacted for 3 h according to general procedure A to afford 13aA (188 mg, 0.82 mmol, 82%) as a colorless oil.
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