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Stereoselective Total Synthesis of Enantiomerically Pure 1‐Trifluoromethyl Tetrahydroisoquinoline Alkaloids
Author(s) -
Bravo Pierfrancesco,
Crucianelli Marcello,
Farina Alessandra,
Meille Stefano Valdo,
Volonterio Alessandro,
Zanda Matteo
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199803)1998:3<435::aid-ejoc435>3.0.co;2-2
Subject(s) - stereocenter , chemistry , tetrahydroisoquinoline , stereoselectivity , trifluoromethyl , stereochemistry , intramolecular force , alkaloid , enantioselective synthesis , enantiomer , organic chemistry , catalysis , alkyl
Enantiomerically pure 1‐trifluoromethyl‐tetrahydroisoquinoline alkaloid analogues, in which C‐1 is a quaternary stereogenic centre, have been synthesized by stereoselective intramolecular Pictet‐Spengler reaction of the N ‐arylethyl γ‐trifluoro‐β‐iminosulfoxide ( R )‐ 3 , and subsequent elaborations of the sulfinyl auxiliary. The absolute stereochemistry of the stereogenic centre was determined by X‐ray diffraction on the α‐phenylpropionic ester (1 R ,2′ S )‐ 10 .