2003
DOI: 10.1016/s0957-4166(03)00398-7
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Memory of chirality in the stereoselective synthesis of β-lactams: importance of the starting amino acid derivative

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Cited by 39 publications
(16 citation statements)
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“…β-Lactam derivatives 12 and 14 were also formed as mixtures of two diastereoisomers at C4. Considering that the memory of chirality favors the formation of 4 S isomers when starting from L-Phe 39 , 41 , 42 , the configuration of the major diastereosiomer was assigned as 4 S .…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…β-Lactam derivatives 12 and 14 were also formed as mixtures of two diastereoisomers at C4. Considering that the memory of chirality favors the formation of 4 S isomers when starting from L-Phe 39 , 41 , 42 , the configuration of the major diastereosiomer was assigned as 4 S .…”
Section: Resultsmentioning
confidence: 99%
“…The configuration was indirectly assigned by the preparation of Ala dipeptide derivatives from 13ab (see supplememntary information for details), and applying the known rule of differential HPLC retention times and chemical shifts of the Ala CH 3 group between homochiral and heterochiral dipeptide derivatives 39,40 . β-Lactam derivatives 12 and 14 were also formed as mixtures of two diastereoisomers at C4. Considering that the memory of chirality favors the formation of 4S isomers when starting from L-Phe 39,41,42 , the configuration of the major diastereosiomer was assigned as 4S.…”
Section: Chemistrymentioning
confidence: 99%
“…In‐depth studies by González‐Muñiz and co‐workers– esthablished that α‐haloamides derived from α‐amino acids were convenient precursors for acceding to this key structural motif in non‐racemic form. Thus, the simple base‐promoted (Cs 2 CO 3 in MeCN) cyclization of some N ‐benzyl‐ N ‐chloroacetyl amino acids provided the expected 1,4,4‐trisubstituted azetidin‐2‐ones in good yields and with ee up to 58 %.…”
Section: Intramolecular α‐Alkylation Of α‐Haloamides: Syntheses Of β‐mentioning
confidence: 99%
“…More recently, it has been noted that the asymmetric induction observed during cyclization of N-alkyl-N-chloroacetyl amino acid derivatives to b-lactams 35 may be ascribed to chirality memory, being dependent on the substituents on the starting material, and can be controlled by the appropriate choice of the base and solvent (Scheme 24.20) [93].…”
Section: Miscellaneousmentioning
confidence: 99%