| Attributs | Valeurs |
|---|
| type
| |
| Is Part Of
| |
| Subject
| |
| Title
| - Nonracemic 3°-Carbamines from the Asymmetric Allylboration ofN-Trimethylsilyl Ketimines with B-Allyl-10-phenyl-9-borabicyclo[3.3.2]decanes
|
| has manifestation of work
| |
| related by
| |
| Author
| |
| Abstract
| - The simple and efficient asymmetric synthesis of 3°-carbamines 7 from N-TMS enamines (3) and either enantiomeric form of β-allyl-10-(phenyl)-9-borabicyclo[3.3.2]decane (1) is reported. The high reactivity (<1 h, −78 °C) and enantioselectivity (60−98% ee) of these substrates can be attributed to the fact that the complexation of 3 with 1 facilitates its isomerization to the corresponding syn-N-TMS ketimine complex from which allylation can occur. In addition to providing the homoallylic amines 7 with predictable stereochemistry, the procedure also permits the efficient recovery of the chiral boron moiety (50−65%) as air-stable crystalline pseudoephedrine complexes 8, which are directly converted back to 1 with allylmagnesium bromide in ether (98%).
|
| article type
| |
| is part of this journal
| |
