132364-41-1

Basic information

• Product Name: (3S)-4-(Benzyloxy)-3-methyl-N-<(R)-α-methyl-4-nitrobenzyl>butanamide
• Synonyms: (3S)-4-(Benzyloxy)-3-methyl-N-<(R)-α-methyl-4-nitrobenzyl>butanamide
• CAS NO: 132364-41-1
• Molecular Weight: 356.422
• Mol File: 132364-41-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3S)-4-(Benzyloxy)-3-methyl-N-<(R)-α-methyl-4-nitrobenzyl>butanamide(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-4-(Benzyloxy)-3-methyl-N-<(R)-α-methyl-4-nitrobenzyl>butanamide(132364-41-1)
• EPA Substance Registry System: (3S)-4-(Benzyloxy)-3-methyl-N-<(R)-α-methyl-4-nitrobenzyl>butanamide(132364-41-1)

Safety Data

• Hazardous Substances Data: 132364-41-1(Hazardous Substances Data)

Upstream product

• 4187-53-5 (R)-2-methyl-p-nitrobenzylamine 
• 64190-49-4 (S)-4-(Benzyloxy)-3-methylbutanoic acid 
• 132437-90-2 (RS)-4-(Benzyloxy)-3-methylbutanoic acid 
• 1838-94-4 isoprene epoxide 
• 132437-89-9 (1E,3RS)-4-(Benzyloxy)-N,N-diethyl-3-methylbut-1-enylamine 
• 64809-19-4 (RS)-4-(Benzyloxy)-3-methylbutanal 
• 132364-34-2 (E)-4-(Diethylamino)-2-methylbut-2-en-1-ol 
• 90809-13-5 (E)-4-(Benzyloxy)-N,N-diethyl-3-methylbut-2-enylamine 
• 90809-23-7 (1E,3S)-4-(Benzyloxy)-N,N-diethyl-3-methylbut-1-enylamine 
• 91458-94-5 (1E,3R)-4-(Benzyloxy)-N,N-diethyl-3-methylbut-1-enylamine 
• 90865-69-3 (3S)-4-Benzyloxy-3-methyl-butyraldehyde 
• 90809-16-8 4-<(E)-4-(Benzyloxy)-3-methylbut-2-enyl>morpholine 
• 90809-27-1 4-<(1E,3R)-4-(Benzyloxy)-3-methylbut-1-enyl>morpholine 
• 132364-36-4 (E)-4-Morpholino-2-methylbut-2-en-1-ol 

Relevant articles and documents

Synthesis of Optically Active Bifunctional Isoprenoid Building Blocks by Rhodium(I)-Catalyzed Asymmetric Allylamine to Enamine Isomerization

The application of the known asymmetric allylamine to enamine isomerization methodology to bifunctional C5-isoprenoid allylic amines of types IId and IIe (Scheme 1) is described.It is shown that a number of such substrates can be isomerized with enantioselectivities of >90percent ee using cationic RhI complexes containing (6,6'-dimethylbiphenyl-2,2'-diyl)bis(diphenylphosphine) (BIPHEMP; 9) as asymmetry-inducing ligand (Scheme 2, Tables 1 and 2).Synthetically most useful is the isomerization of the benzyloxy derivative 10a into the (E)-enamine 11a.This isomerization proceeds with very high enantioselectivity (98-99percent ee) and affords, after enamine hydrolysis, the optically active 4-(benzyloxy)-3-methylbutanals ((R)- or (S)-12) in chemical yields of ca. 90percent.In conjunction, a short synthetic route to the starting material 10a has been developed which has a Pd-catalyzed amination of isoprene epoxide (30) as the key step.Thus, convenient and practical access to the optically active aldehydes (R)- and (S)-12 is now at hand.These aldehydes are useful optically active bifunctional building blocks for isoprenoid homologation.