141268-44-2

Upstream product

• 104-94-9 4-methoxy-aniline 
• 78008-36-3 (R)-2,3-cyclohexylideneglyceraldehyde 
• 139007-45-7 S-(2-Pyridyl) 2-(phenylmethoxy)ethanethioate 
• 141781-23-9 [(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine 

Downstream Products

• 149818-33-7 (+)-(3R,4S)-cis-3-benzyloxy-4-[(S)-1',2'-dihydroxyethyl]-1-(p-methoxyphenyl)-2-azetidinone 
• 149706-06-9 (3R,4S)-4-(Cyclohexylmethylidene)-1-(4-methoxyphenyl)-3-(phenylmethoxy)azetidin-2-one 
• 160237-99-0 (3R,4S)-1-(4-methoxyphenyl)-3-(benzyloxy)-4-(hydroxymethyl)-2-azetidinone 
• 158742-08-6 (3R,4S)-1-(4-Methoxyphenyl)-3-hydroxy-4-(cyclohexylmethyl)-azetidin-2-one 
• 144465-85-0 (3R,4S)-4-(Cyclohexylmethyl)-1-(4-methoxyphenyl)-3-triisopropylsilyloxy-2-azetidinone 
• 144775-26-8 (2R,3R)-3-Benzyloxy-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid 
• 148968-08-5 (+)-(3R,4R)-1-(p-anisyl)-3-benzyloxy-4-formyl-2-azetidinone 

Relevant academic research and scientific papers

Synthesis of β-lactams by condensation of the tin enolates of 2-pyridylthioesters with imines. A comparison between titanium and tin enolates

Addition of triethylamine to a mixture of 2-pyridylthioesters and SnCl4 or SnBr4 affords the corresponding tin(IV) enolates that add to imines to give β-lactams in fair to good yields and with various degree of trans/cis stereoselectivity. Examples of highly diastereofacially selective reactions carried out on a chiral thioester and on a chiral imine are also reported. The results are compared with those obtained in the condensations promoted by TiCl4 and TiBr4.

Highly diastereoselective synthesis of β-lactams by addition of titanium enolates of 2-pyridyl thioesters to chiral imines

Addition of titanium enolates of 2-pyridyl thioesters to chiral imines derived from alkoxy aldehydes occurs with good diastereofacial control, and opens a simple access to important carbapenem antibiotics.