136354-02-4

Upstream product

• 124-41-4 sodium methylate 
• 155396-71-7 tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate 
• 4248-19-5 tert-butyl carbazate 
• 100-52-7 benzaldehyde 
• 865350-17-0 4,4,5,5-tetramethyl-2-(propa-1,2-dien-1-yl)-1,3,2-dioxaborolane 
• 67-56-1 methanol 
• 150884-50-7 benzaldehyde N-boc imine 
• 88000-67-3 tert-butyl benzoylimidocarboxylate 
• 2900-27-8 2-(tert-butoxycarbonylamino)-2-phenylacetic acid 

Downstream Products

• 828253-37-8 (4R,6R)-6-[(3R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yloxy]-4-phenyl-1,3-oxazinan-2-one 
• 1312310-25-0 ethyl 4-[(tert-butoxycarbonyl)amino]-2-oxo-4-phenylbutanoate 
• 1332628-30-4 (4S,6S,4aS,8aR)-acetic acid 7-acetoxymethyl-2-oxo-4-phenyl-hexahydro-pyrano[3,2-e][1,3]oxazin-6-yl ester 

Relevant academic research and scientific papers

Enantioselective, Catalytic Multicomponent Synthesis of Homoallylic Amines Enabled by Hydrogen-Bonding and Dispersive Interactions

We report a one-step catalytic, enantioselective method for the preparation of homoallylic N-Boc amines directly from acetals. Reactive iminium ion intermediates are generated in situ through the combination of an acetal, a chiral thiourea catalyst, trialkylsilyl triflate, and N-Boc carbamate and are subsequently trapped by a variety of allylsilane nucleophiles. No homoallylic ether byproducts are detected, consistent with allylation of the iminium intermediate being highly favored over allylation of the intermediate oxocarbenium ion. Acetals derived from aromatic aldehydes possessing a variety of functional groups and substitution patterns yield homoallylic amines with excellent levels of enantiomeric enrichment. Experimental and computational data are consistent with an anchoring hydrogen-bond interaction between the protioiminium ion and the amide of the catalyst in the enantiodetermining transition state, and with stereodifferentiation achieved through specific noncovalent interactions (NCIs) with the catalyst pyrenyl moiety. Evidence is provided that the key NCI in the major pathway is a π-stacking interaction, contrasting with the cation-πinteractions invoked in previously studied reactions promoted by the same family of aryl-pyrrolidino-H-bond-donor catalysts.

Catalyst-free Mannich-type reaction of 1-(N-acylamino)alkyltriphenylphosphonium salts with silyl enolates

A catalyst-free reaction of 1-(N-acylamino)alkyltriphenylphosphonium tetrafluoroborates with silyl enolates was developed to prepare β-amino carbonyl compounds. The reported method is a useful approach for the preparation of N-protected β-amino esters as

The role of proton shuttling mechanisms in solvent-free and catalyst-free acetalization reactions of imines

Proton transfer is central to the understanding of chemical processes. More so in addition reactions of the type NuH + E → Nu-EH taking place under solvent-free and catalyst-free conditions. Herein we show that the addition of alcohols or amines (the NuH component) to imine derivatives (the E component), in 1:1 ratio, under solvent-free and catalyst-free conditions, are efficient methods to access N,O and N,N-acetal derivatives. In addition, computational studies reveal that they are catalyzed reactions involving two or even three NuH molecules operating in a cooperative manner as H-bonded NuH?(NuH)n?NuH associates (many body effects) in the transition state through a concerted proton shuttling mechanism (addition of alcohols) or stepwise proton shuttling mechanism (addition of amines), thereby facilitating the key proton transfer step.

Synthesis of N-Acyl-N,O-acetals from Aldehydes, Amides and Alcohols

A general synthesis of N-acyl-N,O-acetals from aldehydes, amides and alcohols is reported. This new method consists of two single steps: (a) magnesium-mediated addition of an amide or carbamate to an aldehyde and (b) acid-catalyzed conversion of the N-acylhemiaminal to the N-acyl-N,O-acetal. This two-step protocol allows the multigram synthesis of various N-acyl-O-alkyl-N,O-acetals.

An efficient, practical, and enantioselective method for synthesis of homoallenylamides catalyzed by an aminoalcohol-derived, boron-based catalyst

A practical catalytic method for enantioselective addition of an allene unit to aldimines is disclosed. Transformations are promoted by an in-situ-generated B-based catalyst that is derived from a simple, robust, and readily accessible (in multigram quantities) chiral aminoalcohol. A range of aryl-, heteroaryl-, and alkyl-substituted homoallenylamides can be obtained in 66-91% yield and 84:16 to >99:1 enantiomeric ratio through reactions performed at ambient temperature and in the presence of 0.1-3.0 mol% of the chiral catalyst and a commercially available allenylboron reagent. The catalytic protocol does not require strict anhydrous conditions, can be performed on gram scale, and promotes highly selective addition of an allenyl unit (vs a propargyl group). The utility of the approach is demonstrated through development of succinct approaches to syntheses of anisomycin and epi-cytoxazone.

Catalytic syntheses of γ-functionalized α-keto esters from thioacetals and N,O-acetals

Ethyl 2-(trimethylsilyloxy)acrylic ester (1a) reacts with thioacetals providing the corresponding α-keto-γ-thio esters in good to satisfactory yields. Whereas aminals do not react, N,O-acetals lead to γ-amino-α-keto esters in good to excellent yields. All reactions proceed under mild reaction conditions, and no additional work up is required. Subsequent transformations of the obtained products to the corresponding α-oximes have been demonstrated.

Catalytic asymmetric addition of alcohols to imines: Enantioselective preparation of chiral N,O-aminals

The enantioselective addition of alcohols to imine electrophiles has been shown to proceed in the presence of a catalytic amount of a chiral phosphoric acid catalyst. The reaction allows for the formation of the respective chiral N,O-aminals in excellent yield and enantioselectivity. A total of 11 different alcohols and 11 different imines were successfully used as a clear demonstration of the reaction generality. Copyright

Diastereoselective preparation of novel tetrahydrooxazinones via heterocycloaddition of N-Boc, O-Me-acetals

Under Lewis acid conditions, reaction of N-Boc, O-Me acetals with the (R)-(+)-O-vinyl-pantolactone does not lead to the expected dihydrooxazine, but to the corresponding tetrahydrooxazinone, as a result of the loss of the t-Bu group. A diastereoselective

Preparation of acyclic N-acyl-N,O-acetals by decarboxylation of N-protected α-amino acids and studies of asymmetric amidoalkylation with trimethylsilyl cyanide

Oxidative decarboxylation of N-acyl-α-amino acids with lead tetraacetate followed by treatment with methanol provides a facile method for preparation of acyclic N-acyl-N,O-acetals, which can be used in asymmetric α-amidoalkylation reactions using trimethylsilyl cyanide as nucleophile.