Highly stereoselective cycloadditions of Danishefsky's diene to (-)-8-phenylmenthyl and (+)-8-phenylneomenthyl glyoxylate N-phenylethylimines

• Type: Article in International Scientific Journal
• Date: 2013

Authors

Xerardo Garcia Mera (Author) Other; Maria J Alves (Author) Other; Albertino Goth (Author) Other; Maria Luisa do Vale (Author) FCUP; Jose E Rodriguez Borges (Author) FCUP

Journal

Title: Tetrahedron

Vol. 69

Pages: 2909-2919

ISSN: 0040-4020

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 8 Citations

Scopus - 8 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

CORDIS: Physical sciences > Chemistry > Organic chemistry

Other information

Authenticus ID: P-005-1MZ

DOI: 10.1016/j.tet.2013.02.027

Abstract (EN): Enantiopure 4-oxo-pipecolic acid derivatives were obtained by double asymmetric induction aza-Diels-Alder reactions between chiral glyoxylate N-phenylethylimines and Danishefsky's diene mediated by zinc iodide. The key to success was the use of iminoacetates possessing two chiral auxiliaries, N-(S)- or N-(R)-1-phenylethyl and (-)-8-phenylmenthyl or (+)-8-phenylneomenthyl. Adducts were formed in good yields (78-81%), with complete regioselectivity and high diastereoselectivity (87-96%). The absolute configuration of the adducts formed was unequivocally assigned through NMR, specific optical rotation and X-ray data of appropriated derivatives. These cycloadducts can serve as precursors for bioactive piperidinic azasugars and pipecolic acid derivatives.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 11