87219-30-5

Basic information

• Product Name: (S)-4-(N-benzoylamino)dihydrofuran-2(3H)-one
• Synonyms: (S)-4-(N-benzoylamino)dihydrofuran-2(3H)-one
• CAS NO: 87219-30-5
• Molecular Weight: 205.213
• Mol File: 87219-30-5.mol

Chemical Properties

• CAS DataBase Reference: (S)-4-(N-benzoylamino)dihydrofuran-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-(N-benzoylamino)dihydrofuran-2(3H)-one(87219-30-5)
• EPA Substance Registry System: (S)-4-(N-benzoylamino)dihydrofuran-2(3H)-one(87219-30-5)

Safety Data

• Hazardous Substances Data: 87219-30-5(Hazardous Substances Data)

Upstream product

• 944410-98-4 methyl (S)-3-(benzoylamino)-4-benzoyloxybutanoate 
• 102614-12-0 3(S)-amino-γ-butyrolactone hydrobromide 
• 98-88-4 benzoyl chloride 

Downstream Products

• 87219-35-0 2-phenyl-4(S)-<2-(N,N-dimethylamino)-oxoethyl>-2-oxazolone 
• 102614-13-1 2-phenyl-4(S)-<2-((2-methyl-2-propyl)thio)-2-oxoethyl>-2-oxazoline 
• 87219-33-8 (3S,4S)-3-methyl-4-(N-benzoylamino)dihydrofuran-2(3H)-one 
• 87219-33-8 2(R)-methyl-3(S)-(benzoylamino)-γ-butyrolactone 
• 87219-38-3 (R)-N,N-Dimethyl-3-phenyl-2-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-propionamide 
• 87219-38-3 (S)-N,N-Dimethyl-3-phenyl-2-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-propionamide 
• 87219-38-3 N,N-Dimethyl-3-phenyl-2-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-propionamide 
• 87219-37-2 2-phenyl-4(S)-<3-(N,N-dimethylamino)-3-oxo-2(R)-propyl>-2-oxazoline 
• 87219-37-2 N,N-Dimethyl-2-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-propionamide 
• 87219-33-8 N-((S)-4-Methyl-5-oxo-tetrahydro-furan-3-yl)-benzamide 
• 102614-15-3 2-phenyl-4(S)-<3-((2-methyl-2-propyl)thio)-3-oxo-2(S)-propyl>-2-oxazoline 
• 102614-17-5 2-phenyl-4(S)-(3-oxo-2(R)-pentyl)-2-oxazoline 
• 102614-18-6 2-phenyl-4(S)-(3-oxo-2(S)-pentyl)-2-oxazoline 
• 102614-23-3 (R)-3-((S)-2-Phenyl-4,5-dihydro-oxazol-4-yl)-butan-2-one 

Relevant articles and documents

Asymmetric synthesis of 4-amino-γ-butyrolactones via lithium amide conjugate addition

Upon treatment with homochiral lithium (R)-N-benzyl-N-(α-methylbenzyl)amide, γ-benzyloxy but-2-enoates undergo competitive conjugate addition and γ-deprotonation, while γ-tert-butyldimethylsilyloxy but-2-enoates undergo exclusive conjugate addition. Treatment of γ-benzyloxy or γ-tert-butyldimethylsilyloxy but-2-enamides with lithium (R)-N-benzyl-N-(α-methylbenzyl)amide furnishes exclusively the γ-benzyloxy- or γ-tert-butyldimethylsilyloxy-β-amino amide products of conjugate addition in high de. The γ-tert-butyldimethylsilyloxy-β-amino butanoate products of conjugate addition readily undergo O-desilylation and concomitant cyclisation to furnish 4-[N-benzyl-N-(α-methylbenzyl)amino]-γ-butyrolactone, which may be stereoselectively functionalised via deprotonation and alkylation?to give the corresponding trans-3-alkyl-4-amino-γ-butyrolactones. Alternatively, stereoselective alkylation of γ-benzyloxy- or γ-tert-butyldimethylsilyloxy-β-amino butanoates and butanamides through enolate formation and alkylation following a tandem (via the (Z)-lithium enolate) or stepwise (via the (E)-lithium enolate) protocol gives a range of separable syn- and anti-α-alkyl-β-amino esters and amides. O-Silyl deprotection of the syn- and anti-α-alkyl-β-amino butanoates with TBAF and concomitant cyclisation provide trans-3-alkyl-4-amino-γ-butyrolactones, consistent with epimerisation to the thermodynamically favoured trans-lactone occurring upon deprotection.

DEVELOPMENT OF CHIRAL β-DICARBONYL EQUIVALENTS. ENANTIODIVERGENT ALKYLATION OF ASPARTIC ACID.

L-Aspartic acid has been converted to derivatives which undergo alkylation reactions with stereoselectivities that are enantiomerically complimentary.