title: Expedient synthesis of chiral homoallylamines via N,O-acetal TMS ethers and its application.
abstract: A highly stereoselective and efficient method for the synthesis of optically active homoallylamines was developed. Key features of the method include (1) the utilization of naphthylethylamine as both an excellent chiral auxiliary and the amine source, (2) the 1,3-chiral induction of the N-acyliminium ion with high stereoselectivity and high yield, and (3) facile auxiliary removal under mild conditions to liberate N-Cbz-protected homoallylamines. In addition, the total synthesis of the proposed novel tripeptide containing a β-amino acid has been achieved by applying this method.
authors: College of Pharmacy, Seoul National University, Seoul 151-742, Korea. ygsuh@snu.ac.kr
authors: Young-Ger
authors: YG
authors: Suh
authors: Jaebong
authors: J
authors: Jang
authors: Hwayoung
authors: H
authors: Yun
authors: Sae Mi
authors: SM
authors: Han
authors: Dongyun
authors: D
authors: Shin
authors: Jae-Kyung
authors: JK
authors: Jung
authors: Jong-Wha
authors: JW
authors: Jung
mesh_terms: D000080:Acetals / Q000737:chemistry*; D000499:Allylamine / Q000138:chemical synthesis*; D004986:Ether / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D000080:Acetals; D010455:Peptides; D014297:Trimethylsilyl Compounds; D004986:Ether; D000499:Allylamine