LEWIS ACID-PROMOTED 1,4-ADDITION TO CHIRAL IMIDE DERIVATIVES IN THE SYNTHESIS OF BETA-AMINO ACIDS
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AMOROSO, R
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UNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,CTR STUDIO FIS MACROMOLEC,I-40126 BOLOGNA,ITALYUNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,CTR STUDIO FIS MACROMOLEC,I-40126 BOLOGNA,ITALY
AMOROSO, R
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CARDILLO, G
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UNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,CTR STUDIO FIS MACROMOLEC,I-40126 BOLOGNA,ITALYUNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,CTR STUDIO FIS MACROMOLEC,I-40126 BOLOGNA,ITALY
CARDILLO, G
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SABATINO, P
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UNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,CTR STUDIO FIS MACROMOLEC,I-40126 BOLOGNA,ITALYUNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,CTR STUDIO FIS MACROMOLEC,I-40126 BOLOGNA,ITALY
SABATINO, P
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TOMASINI, C
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UNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,CTR STUDIO FIS MACROMOLEC,I-40126 BOLOGNA,ITALYUNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,CTR STUDIO FIS MACROMOLEC,I-40126 BOLOGNA,ITALY
TOMASINI, C
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TRERE, A
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UNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,CTR STUDIO FIS MACROMOLEC,I-40126 BOLOGNA,ITALYUNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,CTR STUDIO FIS MACROMOLEC,I-40126 BOLOGNA,ITALY
TRERE, A
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[1] UNIV BOLOGNA,DIPARTIMENTO CHIM G CIAMICIAN,CTR STUDIO FIS MACROMOLEC,I-40126 BOLOGNA,ITALY
The 1,4-addition of O-benzylhydroxylamine to imides 3 in the presence of various Lewis acids is described. The reaction is performed in CH2Cl2 at -78-degrees-C and affords derivatives 4 and 5 in good chemical yields and in different diastereomeric ratios, depending on the Lewis acid employed. TiCl4 and Me2AlCl give opposite diastereoselectivities. Furthermore, enantiomerically pure beta-amino acid 9 is obtained in good yield from compound 4a.
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页码:5615 / 5619
页数:5
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STEIGER RE, 1955, ORGANIC SYNTHESIS CO, V3, P664