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A De Novo Stereocontrolled Approach to syn ‐ and anti ‐Disubstituted Acyclic β 2,3 ‐Amino Acid Enantiomers
Author(s) -
Cherepanova Maria,
Kiss Loránd,
Forró Enikő,
Fülöp Ferenc
Publication year - 2014
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/ejoc.201301281
Subject(s) - enantiopure drug , chemistry , stereoselectivity , cyclopentene , enantiomer , stereochemistry , bicyclic molecule , wittig reaction , bond cleavage , enantioselective synthesis , organic chemistry , catalysis
The stereocontrolled syntheses of functionalized acyclic β 2,3 ‐amino acid derivatives in enantiomerically pure form were performed by starting from enantiopure cis‐ and trans ‐2‐aminocyclopent‐3‐enecarboxylates, which were derived from a racemic bicyclic β‐lactam. The synthetic strategy involves the stereoselective dihydroxylaton of the C–C double bond of the cyclopentene β‐amino esters. The subsequent NaIO 4 ‐mediated ring cleavage affords dialdehyde intermediates that undergo functionalization by a Wittig reaction.