Synthesis of Chiral 1,4,2-Oxazaphosphepines

Salgado-Escobar, Oscar; Chavelas‐Hernández, Leticia; Domínguez-Mendoza, Blanca Eda; Linzaga-Elizalde, Irma; Ordóñez, Mario

doi:10.3390/molecules200813794

Cited by 8 publications

(3 citation statements)

References 26 publications

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“…Thus, reaction of (2S,3S,5S,6R)-107 with catalytic amounts of potassium tert-butoxide in CH2Cl2 at room temperature followed by the addition of methyl cinnamate, gave the cyclic α-amino-Cphosphinate (2S,3S,5S,6R)-108 in 92% yield and with 70% diastereoisomeric excess (Scheme 47). On the other hand, Ordóñez et al [97] carried out the stereoselective synthesis of novel 1,4,2-oxazaphosphepines from chiral 1,3-benzoxazines. For this purpose, the reaction of the chiral 1,3-benzoxazines 109a-d with dichlorophenylphosphine in the presence of Et3N in CH2Cl2 at room temperature, gave the 1,4,2-oxazaphosphepines 110a-d in 50:50 to 100:0 diastereoisomeric ratio.…”

Section: 42-oxazaphosphacyclesmentioning

confidence: 99%

“…The configuration assignment was stablished by X-ray analysis of final products. On the other hand, Ordóñez et al [97] carried out the stereoselective synthesis of novel 1,4,2-oxazaphosphepines from chiral 1,3-benzoxazines. For this purpose, the reaction of the chiral 1,3-benzoxazines 109a-d with dichlorophenylphosphine in the presence of Et 3 N in CH 2 Cl 2 at room temperature, gave the 1,4,2-oxazaphosphepines 110a-d in 50:50 to 100:0 diastereoisomeric ratio.…”

Section: 42-oxazaphosphacyclesmentioning

confidence: 99%

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Stereoselective Synthesis of α-Amino-C-phosphinic Acids and Derivatives

et al. 2016

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α-Amino-C-phosphinic acids and derivatives are an important group of compounds of synthetic and medicinal interest and particular attention has been dedicated to their stereoselective synthesis in recent years. Among these, phosphinic pseudopeptides have acquired pharmacological importance in influencing physiologic and pathologic processes, primarily acting as inhibitors for proteolytic enzymes where molecular stereochemistry has proven to be critical. This review summarizes the latest developments in the asymmetric synthesis of acyclic and phosphacyclic α-amino-C-phosphinic acids and derivatives, following in the first case an order according to the strategy used, whereas for cyclic compounds the nitrogen embedding in the heterocyclic core is considered. In addition selected examples of pharmacological implications of title compounds are also disclosed.

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Section: 42-oxazaphosphacyclesmentioning

confidence: 99%

Section: 42-oxazaphosphacyclesmentioning

confidence: 99%

Stereoselective Synthesis of α-Amino-C-phosphinic Acids and Derivatives

et al. 2016

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“…Considering the high value of these compounds and in connection with our recent work [33], we report herein an innovative methodology for the synthesis of secondary phosphonates and α-aminophosphonates from the reaction of 1,3-benzoxazines with diethyl or triethyl phosphite using catalytic amounts of boron trifluoride etherate. In addition, when the 1,3-benzoxazines was treated with alcohols under reflux conditions provided the corresponding ethers in good yields.…”

Section: Introductionmentioning

confidence: 99%

Direct Synthesis of Phosphonates and α-Amino-phosphonates from 1,3-Benzoxazines

et al. 2019

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A straightforward and novel method for transformation of readily available 1,3-benzoxazines to secondary phosphonates and α-aminophosphonates using boron trifluoride etherate as catalyst is developed. The formation of phosphonates proceeds through ortho-quinone methide (o-QM) generated in situ, followed by a phospha-Michael addition reaction. On the other hand, the α-aminophosphonates were obtained by iminium ion formation and the subsequence nucleophilic substitution of alkylphosphites. This method can be also used for the preparation of o-hydroxybenzyl ethers through oxa-Michael addition.

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Furan Ring Opening – Pyridine Ring Closure: An Efficient Approach towards 6H‐Isochromeno[4,3‐b]pyridin‐6‐ones from Readily Available Furans and Phthalaldehydic Acid Methyl Esters

et al. 2018

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An efficient iodine‐catalyzed three‐component Mannich‐type reaction of various 2‐alkylfurans, methyl 2‐formylbenzoates and carbamates under mild reaction conditions was realized. Synthetic utility of the resulting N‐Boc‐1‐[2‐(carbomethoxy)aryl]furfurylamines was demonstrated by their facile two‐step transformation into 2‐methyl‐6H‐isochromeno[4,3‐b]pyridin‐6‐ones, which are employed in high‐performance cyclometalated OLEDs.

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Synthesis of Chiral 1,4,2-Oxazaphosphepines

Cited by 8 publications

References 26 publications

Stereoselective Synthesis of α-Amino-C-phosphinic Acids and Derivatives

Stereoselective Synthesis of α-Amino-C-phosphinic Acids and Derivatives

Direct Synthesis of Phosphonates and α-Amino-phosphonates from 1,3-Benzoxazines

Furan Ring Opening – Pyridine Ring Closure: An Efficient Approach towards 6H‐Isochromeno[4,3‐b]pyridin‐6‐ones from Readily Available Furans and Phthalaldehydic Acid Methyl Esters

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