Journal
TETRAHEDRON LETTERS
Volume 57, Issue 17, Pages 1903-1905Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2016.03.063
Keywords
Borate; Imine; Sulfinamide; Condensation
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Triisopropyl borate effects the condensation of aldehydes with sulfinamides to give N-sulfinyl imines. The reaction is amenable to 1 degrees, 2 degrees, and 3 degrees alkyl aldehydes, as well as aryl, heteroaryl, and alpha,beta-unsaturated aldehydes. In addition to tert-butanesulfinanide, the condensation is also effective with 4-toluenesulfinamide and 2,4,6-triisopropylphenylsulfinamide. This protocol proceeds under homogeneous reaction conditions and requires no post-reaction filtration of insoluble reagents or byproducts. (C) 2016 Elsevier Ltd. All rights reserved.
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