130748-67-3

Upstream product

• 51220-84-9 (S)-methyl 4-methyl-2-(4-methylphenylsulfonamido)pentanoate 
• 7533-40-6 (S)-2-amino-4-methylpentan-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 1220-80-0 (S)-4-methyl-2-(toluene-4-sulfonamido)pentanoic acid 
• 124-38-9 carbon dioxide 
• 61-90-5 L-leucine 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 7517-19-3 methyl (L)-leucinate hydrochloride 

Downstream Products

• 124575-31-1 (S)-2-isobutyl-1-tosyl-aziridine 
• 936012-04-3 (S)-N-(1-cyano-4-methylpentan-2-yl)-4-methylbenzenesulfonamide 
• 863403-26-3 (+)-(S)-(E)-6-methyl-4-(4-methylbenzylamino)hept-2-en-1-ol 
• 863403-34-3 N-(4-hydroxy-1-isobutyl-but-2-enyl)-N-(4-methyl-benzyl)-2-(toluene-4-sulfonyl)-acetamide 
• 863403-32-1 (-)-(S)-(E)-carbonic acid methyl ester 6-methyl-4-{(4-methylbenzyl)-[2-(toluene-4-sulfonyl)acetyl]amino}hept-2-enyl ester 
• 220306-76-3 (-)-(S)-(E)-6-methyl-4-(toluene-4-sulfonamido)hept-2-en-1-ol 
• 247200-54-0 Ethyl (4S,2E)-6-methyl-4-[(4-methylphenylsulfonyl)amino]hept-2-enoate 
• 678166-32-0 (4S,2E)-2,6-dimethyl-4-[N-(4-methylphenylsulfonyl)amino]hept-2-en-1-ol 
• 678166-26-2 methyl (4S,2E)-2,6-dimethyl-4-[N-(4-methylphenylsulfonyl)amino]hept-2-enoate 
• 678166-37-5 (4S,2E)-O-methoxycarbonyl-2,6-dimethyl-4-[N-(4-methylphenylsulfonyl)amino]hept-2-en-1-ol 
• 678166-51-3 (4S,2E)-2,6-dimethyl-4-[N-(4-methylphenylsulfonyl)amino]-O-methylsulfonylhept-2-en-1-ol 
• 1352166-01-8 (S)-N-allyl-N-(4-methylbenzenesulfonyl)-leucinol 

Relevant academic research and scientific papers

Two rearrangement pathways in the geminal acylation of 2-methoxyoxazolidines leading to substituted 1,4-oxazines

Lewis acid-mediated geminal acylation of 2-methoxyoxazolidines with five- or six-membered acyloins followed by heterocyclization afforded 1,4-oxazines fused to cyclopentenone or cyclohexenone rings. Overall yields ranged from 30 to 73%. The position of the carbonyl group in the products depended on whether or not water was present during the ringexpanding acyl migration step. The route lacking water during the acyl migration step was best conducted in one pot. The addition of water effected cleavage of a silyloxy group in the intermediate during the initial Mukaiyama aldol reaction prior to the acyl migration.

Highly exo selective, photochemically promoted cyclization of iodoallene derivatives

A photochemically promoted intramolecular cyclization of aryl-, vinyl-, and alkyliodo allenes has been developed. The optimal conditions employed [Ir(ppy)2(dtbbpy)]PF6 (1?mol%) as catalyst affording products with high exo selectivity in moderate to good yields. Chiral substrates showed diastereoselectivity of up to 95/5 favoring trans product.

Enantio- and Regioselective Palladium(II)-Catalyzed Dioxygenation of (Aza-)Alkenols

An oxidative Pd-catalyzed intra-intermolecular dioxygenation of (aza-)alkenols has been reported, with total regioselectivity. To study the stereoselectivity, different chiral ligands as well as different hypervalent-iodine compounds have been compared. I

Synthesis and hetero-Diels-Alder reactions of enantiomerically pure dihydro-1: H -azepines

Thermolysis of enantiomerically pure 3-substituted 7,7-dihalo-2-azabicyclo[4.1.0]heptanes in the presence of K2CO3 gives in good yields 2-alkyl-6-halo-1-tosyl-2,3-dihydro-1H-azepines. These undergo highly stereoselective [4+2] cycloaddition reactions with heterodienophiles and arylation/alkenylation under Suzuki conditions.

Selective 7- endo -Cyclization of 3-Aza-5-alkenols through Oxidative Pd(II)-Catalyzed Olefin Oxyarylation

3-Aza-5-alkenols undergo selective 7- endo - trig cyclization when treated with a catalytic Pd(II) species, CuCl 2 and ArSnBu 3 giving 7-aryl-substituted oxazepanes. The intramolecular alkoxylation occurs with formation of a seven-me

An efficient synthetic approach for N-C bond formation from (S)-amino acids: An easy access to cis-2,5-disubstituted chiral piperazines

An efficient synthetic strategy is described for the construction of amino acids derived enantiomerically pure cis-2,5-disubstituted chiral piperazines. Cu-catalyzed spontaneous regioselective ring opening and ring closing of non-activated N-tosyl aziridines as well as Pd-mediated N-C bond formation from N-tosyl halogenated amino-derivatives are the key steps for accessing disubstituted piperazines.

A mild multistep conversion of n-protected α-amino acids into N-protected β3-amino acids utilizing the Nef reaction

Current methods of homologation of α-amino acids to β-amino acids have limitations. To overcome these shortfalls the Nef reaction has been utilized in the multistep synthesis of β3-amino acids from α-amino acids. In this approach, N-protected a

Regioselective ring-opening of amino acid-derived chiral aziridines: An easy access to cis-2,5-disubstituted chiral piperazines

An efficient four-step synthetic strategy for cis-2,5-disubstituted chiral piperazines derived from amino-acid-based aziridines is described. The key steps in this strategy are the highly regioselective boron trifluoride diethyl etherate (BF3·OEt2)-mediated ring-opening of less-reactive N-Ts chiral aziridines by α-amino acid methyl ester hydrochloride followed by Mitsunobu cyclization. This protocol has been used in an attempt to construct the piperazine core framework of natural product (+)-piperazinomycin. The pied piperazines: A four-step efficient synthetic strategy for cis-2,5-disubstituted chiral piperazines derived from amino acid-based aziridines is described. The key reaction steps are the highly regioselective BF3·OEt2 mediated ring-opening of less-reactive N-Ts chiral aziridines by α-amino acid methyl ester hydrochlorides, followed by a Mitsunobu cyclization. This protocol has been used in an attempt to construct the piperazine core framework of natural product (+)-piperazinomycin. Copyright

Gold-catalyzed direct activation of allylic alcohols in the stereoselective synthesis of functionalized 2-vinyl-morpholines

Alcohol versus alcohol: A highly stereocontrolled synthesis of substituted morpholines is realized by means of gold-catalyzed dehydrative allylic cyclization of diols (see scheme for one example; segphos = 5,5′-bis[di(3, 5-di-tert-butyl-4-methyoxyphenyl)phosphine]-4,4′-bi-1,3-benzodioxole). The present methodology represents one of the few examples of enantioselective gold-catalyzed transformations involving unactivated alkenes. Copyright

Asymmetric Strecker reaction of N-benzhydrylimines utilising new tropos biphenyldiol-based ligands

The synthesis of a library of N-arenesulfonyl-1,3-oxazolidinyl-substituted biphenyldiols is presented. A set of two central intermediates together with easily accessible N-arenesulfonylamino alcohols furnish a broad variety of 1,3-oxazolidines. These are applied as chiral tropos ligands in a titanium-mediated Strecker-type reaction of N-benzhydrylimines. A correlation between the ee values in the product and the diastereomeric ratio concerning the chiral axis of the ligand is made. Those substituents in the ligand which proved to lead to a higher preference for one diastereomeric conformer of the chiral axis in related compounds now provide the most selective ligands. Two privileged ligands are identified that afford superior results in 8 of 13 screenings. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.