The first stereoselective synthesis of chiral halogenophosphines: optically active tert-butyl(phenyl)chlorophosphine

1992 ◽  
pp. 1718-1719 ◽  
Author(s):  
Jan Omelańczuk
Keyword(s):  
Stereoselective Synthesis ◽  
Optically Active ◽  
Tert Butyl

Stereoselective synthesis of optically active cyclopenta[c]pyridines and tetrahydropyridines

2012 ◽  
Vol 23 (9) ◽  
pp. 662-669 ◽  
Author(s):  
Serdar Sezer ◽  
Yasemin Gümrükçü ◽  
İrem Bakırcı ◽  
M. Yağız Ünver ◽  
Cihangir Tanyeli
Keyword(s):  
Stereoselective Synthesis ◽  
Optically Active

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.

A new approach to the stereoselective synthesis of trans-3-carbamoyl-β-lactam moieties

2017 ◽  
Vol 41 (6) ◽  
pp. 2479-2489 ◽  
Author(s):  
Anna Zakaszewska ◽  
Ewelina Najda-Mocarska ◽  
Sławomir Makowiec
Keyword(s):  
Stereoselective Synthesis ◽  
Optically Active ◽  
Thermal Generation ◽  
New Approach

Optically active 1,4-disubstituted-3-carbamoyl-azetidinones are synthesized from 5-[(N-arylamino)(hydroxyl)methylene]-2,2-dimethyl-1,3-dioxa-4,6-diones and chiral aldimines via thermal generation of carbamoyl ketenes and subsequent [2+2] cycloaddition.

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