82912-16-1Relevant articles and documents
Asymmetric Propargylboration of Aldimines and Ketimines with the Borabicyclo[3.3.2]decanes: Novel Entries to Allenyl Carbinamines, Amino Acids, and Their α-Methyl Counterparts
Alicea-Matías, Eyleen,Soderquist, John A.
, p. 336 - 339 (2017)
Available in either enantiomerically pure form through quantitative Grignard procedures from air-stable crystalline complexes (1, 3), the B-γ-TMS propargylic derivatives of the 10-TMS- (2) and 10-phenyl-9-borabicyclo[3.3.2]decanes (4) provide highly selec
Nonracemic 3°-carbamines from the asymmetric allylboration of N-trimethylsilyl ketimines with B-allyl-10-phenyl-9-borabicyclo[3.3.2]decanes
Canales, Eda,Hernandez, Eliud,Soderquist, John A.
, p. 8712 - 8713 (2007/10/03)
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%). Copyright
