317359-30-1Relevant academic research and scientific papers
Synthesis of highly substituted 2-spiropiperidines
Griggs, Samuel D.,Thompson, Nathan,Tape, Daniel T.,Fabre, Marie,Clarke, Paul A.
, p. 6663 - 6674 (2018/09/29)
2-Spiropiperidines are a highly desirable, yet under represented structure in drug discovery. 2-Spiropiperidines were synthesised in either a two-pot or one-pot reaction. In the two-pot reaction, the addition of a Weiler dianion to N-Boc imines, followed by deprotection and in situ condensation with a cyclic ketone generated functionalised 2-spiropiperidines in good to excellent yields. In the one-pot reaction, the addition of Chan's diene to N-Boc imines under Maitland-Japp conditions, followed by the addition of sodium bicarbonate and a cyclic ketone formed functionalised 2-spiropiperidines in moderate to good yields.
Efficient synthesis of α-(N-Boc)aminoamides by addition of a carbamoylsilane to N-Boc-imines
Guo, Qilin,Wen, Xueping,Chen, Jianxin
, p. 8117 - 8122 (2016/11/19)
N,N-Dimethylcarbamoyl(trimethyl)silane reacted with N-Boc-imines in anhydrous benzene under catalysts-free conditions to afford N-Boc-protected α-amino amides in good yields (72-89%). The electronic property and the steric hindrance of substituent on the N-Boc-imines affected the reaction.
Enantioselective Mannich reaction of β-keto esters with aromatic and aliphatic imines using a cooperatively assisted bifunctional catalyst
Neuvonen, Antti J.,Pihko, Petri M.
supporting information, p. 5152 - 5155 (2015/01/08)
An efficient urea-enhanced thiourea catalyst enables the enantioselective Mannich reaction between β-keto esters and N-Boc-protected imines under mild conditions and minimal catalyst loading (1-3 mol %). Aliphatic and aromatic substituents are tolerated on both reaction partners, affording the products in good enantiomeric purity. The corresponding β-amino ketones can readily be accessed via decarboxylation without loss of enantiomeric purity.
