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Regio‐ and Stereoselective Opening of Oxiranes through Neighbouring Group Participation: Stereocontrolled Synthesis of Enantiopure Hydroxylated Oxazolidin‐2‐ones
Author(s) -
Langlois Nicole,
Moro Alberto
Publication year - 1999
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(199912)1999:12<3483::aid-ejoc3483>3.0.co;2-e
Subject(s) - aminolysis , enantiopure drug , chemistry , stereoselectivity , stereochemistry , yield (engineering) , ring (chemistry) , epoxide , group (periodic table) , alkoxy group , organic chemistry , enantioselective synthesis , catalysis , alkyl , materials science , metallurgy
The regio‐ and stereo‐selective ring opening of ( S )‐pyroglutaminol derived epoxides provides an effective route to protected syn,syn ‐aminodiol units. The procedure involves the chemoselective aminolysis or alcoholysis of (3 R ,4 R ,5 R ) ‐N ‐( tert ‐butoxycarbonyl)‐3,4‐epoxy‐5‐[(1‐ethoxy)ethoxymethyl]pyrrolidin‐2‐one ( 10 ), followed by the formation in quantitative yield of oxazolidinone intermediates, through the mediation of neighbouring N ‐Boc groups. The practical synthetic interest of this route is illustrated by the example of (3 R ,4 S ,5 R )‐3,4‐diacetoxy‐5‐(acetoxymethyl)pyrrolidin‐2‐one which should serve as useful building block in further syntheses.