scholarly journals Highly Enantioselective Synthesis of (2S)-α-(Hydroxymethyl)-glutamic Acid by the Catalytic Michael Addition of 2-Naphthalen-1-yl-2-oxazoline-4-carboxylic Acid tert-Butyl Ester.

ChemInform ◽  
2005 ◽  
Vol 36 (48) ◽  
Author(s):  
Yeon-Ju Lee ◽  
Jihye Lee ◽  
Mi-Jeong Kim ◽  
Byeong-Seon Jeong ◽  
Jeong-Hee Lee ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Glutamic Acid ◽  
Michael Addition ◽  
Butyl Ester ◽  
Enantioselective Synthesis ◽  
Tert Butyl

Highly Enantioselective Synthesis of (2S)-α-(Hydroxymethyl)-glutamic Acid by the Catalytic Michael Addition of 2-Naphthalen-1-yl-2-oxazoline-4-carboxylic Acidtert-Butyl Ester

2005 ◽  
Vol 7 (15) ◽  
pp. 3207-3209 ◽  
Author(s):  
Yeon-Ju Lee ◽  
Jihye Lee ◽  
Mi-Jeong Kim ◽  
Byeong-Seon Jeong ◽  
Jeong-Hee Lee ◽  
...  
Keyword(s):  
Glutamic Acid ◽  
Michael Addition ◽  
Butyl Ester ◽  
Enantioselective Synthesis

Synthesis of Optically Active Hydroxyalkyl Cycloheptatrienes: A Key Step in the Total Synthesis of 6,11-Methylene-LXB4

Synlett ◽  
2020 ◽  
Vol 32 (01) ◽  
pp. 45-50
Author(s):  
Udo Nubbemeyer ◽  
Analuisa Nava ◽  
Lukas Trippe ◽  
Andrea Frank ◽  
Lars Andernach ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Total Synthesis ◽  
Structure Elucidation ◽  
Butyl Ester ◽  
Optically Active ◽  
Chiral Hplc ◽  
Reaction Conditions ◽  
Acid Product ◽  
Tert Butyl ◽  
Nabh4 Reduction

AbstractStarting from methyl cycloheptatrienyl-1-carboxylate, 6-acylation was successfully achieved employing glutaryl chloride in the presence of AlCl3 under controlled reaction conditions to furnish keto carboxylic acid product. After protection of this keto carboxylic acid as tert-butyl ester, reagent-controlled enantioselective reductions delivered configuration-defined methyl-6-hydroxylalkyl cycloheptatriene-1-carboxylates with up to 80% ee. Whereas simple NaBH4 reduction of the keto carboxylic acid and subsequent lactonization afforded a methyl-6-tetrahydropyranonyl cycloheptatriene-1-carboxylate. Resolution using chiral HPLC delivered the product enantiomers with up to >99% ee Finally, ECD analyses enabled structure elucidation. The products are used as key intermediates in enantioselective 6,11-methylene-lipoxin B4 syntheses.

scholarly journals Crystal structure of 2-(4-allyl-4-methyl-2-oxo-1,4-dihydro-2H-benzo[d]- [1,3]oxazin-6-yl)-5-cyano-pyrrole-1-carboxylic acid tert-butyl ester, C22H23N3O4

2014 ◽  
Vol 229 (2) ◽  
pp. 127-128 ◽  
Author(s):  
Chuanhong Zhang ◽  
Jianguo Lin ◽  
Gaochao Lv ◽  
Yang Cao ◽  
Shineng Luo
Keyword(s):  
Crystal Structure ◽  
Carboxylic Acid ◽  
Butyl Ester ◽  
Tert Butyl

Abstract C22H23N3O4, triclinic, P1¯ (no. 2), a = 6.992(3) Å, b = 8.159(4) Å, c = 18.778(8) Å, α = 92.118(7)°, β = 93.463(7)°, γ = 101.623(7)°, V = 1045.9 Å3, Z = 2, Rgt(F) = 0.0576, wRref(F2) = 0.1778, T = 296 K.

ChemInform Abstract: Synthesis and Cytotoxic Activity of Derivatives of the tert-Butyl Ester of 7Z-Acetylmethylene-3-methyl-3-cephem-4-carboxylic Acid

ChemInform ◽  
2009 ◽  
Vol 40 (47) ◽  
Author(s):  
I. Potorocina ◽  
M. Vorona ◽  
G. Veinberg ◽  
I. Shestakova ◽  
I. Kanepe ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Cytotoxic Activity ◽  
Butyl Ester ◽  
Tert Butyl ◽  
Derivatives Of
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