ChemInform Abstract: Diastereo- and Enantioselective Synthesis of β-Amino Cyclic Ethers via the Intramolecular Reaction of γ-Alkoxyallylstannane with Imine

Autor:	Yoshinori Yamamoto, Jung Youl Park, Isao Kadota
Rok vydání:	2010
Předmět:	chemistry.chemical_compound Chiral auxiliary chemistry Intramolecular reaction Stereochemistry Imine Enantioselective synthesis Diastereomer General Medicine Lewis acids and bases Chiral Lewis acid Enantiomeric excess
Zdroj:	ChemInform. 30
ISSN:	1522-2667 0931-7597
Popis:	The intramolecular Lewis acid mediated cyclization of γ-alkoxyallylstannanes 1, 2, and 14, bearing a hydrazone group at the terminus of the carbon chain, afforded exclusively the corresponding trans β-amino cyclic ethers 3a, 4a, and 15, respectively. The Lewis acid mediated cyclization of γ-alkoxyallylstannane 5, having (R)-(+)-1-phenylethylamine as a chiral auxiliary, afforded exclusively trans β-amino cyclic ether 6a with very high diastereomeric excess (de) in very high chemical yields. The asymmetric cyclization of γ-alkoxyallylstannane with imine 7 in the presence of chiral titanium−BINOL complex 9, afforded predominantly cis β-amino cyclic ether 8b with high enantiomeric excess (ee). The chiral Lewis acid mediated cyclization of racemic compound 38 containing phenyl as a substituent afforded cis isomer 39 with very high enantiomeric excess (ee).
Databáze:	OpenAIRE
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