Palladium-catalyzed asymmetric allylic substitution using novel phosphino-ester (PHEST) ligands with 1,1′-binaphthyl skeleton

Autor:	Tetsuo Ohta, Isao Furukawa, Toshiji Taiji, Hidehiko Kodama
Rok vydání:	2000
Předmět:	Allylic rearrangement Trimethylsilyl Stereochemistry Organic Chemistry Chiral ligand Dimethyl malonate Catalysis Inorganic Chemistry chemistry.chemical_compound Tsuji–Trost reaction chemistry Physical and Theoretical Chemistry Potassium phthalimide Acetamide Amination
Zdroj:	Tetrahedron: Asymmetry. 11:4009-4015
ISSN:	0957-4166
DOI:	10.1016/s0957-4166(00)00370-0
Popis:	The asymmetric allylic alkylation of rac -1,3-diphenyl-2-propenyl acetate 1 with dimethyl malonate 2a proceeded smoothly in the presence of lithium acetate, BSA ( N , O -bis(trimethylsilyl)acetamide), [Pd(η 3 -C 3 H 5 )Cl] 2 , and the chiral ligand ( R )- i -Pr 2 N-PHEST ( R )- 5a to give the allylic alkylation product ( R )- 3a in 89% yield with 99% ee. Furthermore, the asymmetric allylic amination of 1 with potassium phthalimide 2c has been carried out using the same ligand to give the allylic amination product ( S )- 3c in 10% yield with 66% ee.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::6b4af7380e70b778851d775484e7421b https://doi.org/10.1016/s0957-4166(00)00370-0 Zobrazit plný text záznamu Full Text from ScienceDirect