ChemInform Abstract: Synthesis of 1,3-Thiazolidines from Aromatic Thioketones and N-Benzylidene α-Amino Acid Esters via 1,3-Dipolar Cycloaddition of Azomethine Ylides.

ChemInform ◽  
2010 ◽  
Vol 32 (26) ◽  
pp. no-no
Author(s):  
Andreas Gebert ◽  
Anthony Linden ◽  
Heinz Heimgartner
Keyword(s):  
Amino Acid ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Amino Acid Esters ◽  
Acid Esters

Diastereoselective 1,3-Dipolar Cycloadditions and Michael Reactions of Azomethine Ylides to (2R)-3-Benzoyl-4-methylidene-2-phenyloxazolidin-5-one and (2S)-3-Benzoyl-2-t-butyl-4-methylideneoxazolidin-5-one

1998 ◽  
Vol 51 (2) ◽  
pp. 137 ◽  
Author(s):  
Stephen G. Pyne ◽  
Javad Safaei-G. ◽  
Karl Schafer ◽  
Abdollah Javidan ◽  
Brian W. Skelton ◽  
...  
Keyword(s):  
Amino Acid ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Amino Acid Esters ◽  
Dipolar Cycloadditions ◽  
Michael Reactions ◽  
Michael Adducts ◽  
Practical Synthesis ◽  
The Michael Addition ◽  
Acid Esters

The 1,3-dipolar cycloaddition reactions of (1) and (11) with the azomethine ylides derived from N-benzylidene α-amino acid esters (2) proceed with good to high exo-diastereoselectivity giving the cycloadducts (4) and (12), respectively. The cycloaddition adducts can be converted to highly functionalised prolines (14), (15) and (17) in high enantiomeric purities. The Michael addition adducts of (1) and (11) with the azomethine ylides derived from the N-(disubstituted methylidene) α-amino acid esters (18), (19) and (33) allow for a practical synthesis of all four stereoisomers of 4-benzamidopyroglutamate. The stereochemistry of these cycloaddition and Michael adducts has been extensively determined by single-crystal X-ray structural analysis [compounds (4b), (5b,d), (12b,d), (13e), (15), (20), (21) and (27)]. Lithium-chelated transition state structures have been proposed to rationalize the stereochemical outcomes of these reactions.

Pyrrolidine ring formation by a new base-promoted 1,3-dipolar cycloaddition of N-(phenylthiomethyl) amino acid esters

1984 ◽  
Vol 25 (15) ◽  
pp. 1579-1582 ◽  
Author(s):  
Nobuyuki Imai ◽  
Yoshiyasu Terao ◽  
Kazuo Achiwa ◽  
Minoru Sekiya
Keyword(s):  
Amino Acid ◽  
Ring Formation ◽  
Dipolar Cycloaddition ◽  
Amino Acid Esters ◽  
Pyrrolidine Ring ◽  
Acid Esters

scholarly journals Pyrrolidine-forming 1,3-dipolar cycloaddition of N-(phenylthiomethyl)-.ALPHA.-amino acid esters.

1986 ◽  
Vol 34 (3) ◽  
pp. 1080-1088 ◽  
Author(s):  
NOBUYUKI IMAI ◽  
MARI NEMOTO ◽  
YOSHIYASU TERAO ◽  
KAZUO ACHIWA ◽  
MINORU SEKIYA
Keyword(s):  
Amino Acid ◽  
Dipolar Cycloaddition ◽  
Amino Acid Esters ◽  
Alpha Amino Acid ◽  
Acid Esters

ChemInform Abstract: Pyrrolidine Forming 1,3-Dipolar Cycloaddition of N-(Phenylthiomethyl)-α-amino Acid Esters.

1986 ◽  
Vol 17 (36) ◽  
Author(s):  
N. IMAI ◽  
M. NEMOTO ◽  
Y. TERAO ◽  
K. ACHIWA ◽  
M. SEKIYA
Keyword(s):  
Amino Acid ◽  
Dipolar Cycloaddition ◽  
Amino Acid Esters ◽  
Acid Esters
Sign in / Sign up

Export Citation Format

Share Document