LAP Lambert Academic Publishing ( 2010-10-14 )
€ 49,00
The enantiomerically pure pyrrolidine diester (Ring A) is a useful building block for the synthesis of chiral tolyporphin and other hydroporphyrin compounds. This was synthesized from enantiomerically pure lactam-lactone. Treatment of optically active aromatic amines with bislactone gave pairs of N-alkylated lactam-lactone diastereomers. These diastereomers were separated by MPL chromatography and debenzylated using ceric (IV) ammonium nitrate (CAN) to yield enantiomerically pure lactam-lactone isomers. The (–)-lactam-lactone enantiomer was treated with methanolic cyanide solution which selectively opened lactone ring to form the cyano lactam. This was further transformed into the cis- and trans-thiocyanolactam isomers. The configurations of these isomers were established by NOE experiment which was confirmed by X-ray measurement and theoretical means(ab initio calculations). Coupling of cis-thiocyanolactam with bromomalonic diester according to the sulphide contraction method gave the enantiomerically pure pyrrolidine diester.
Book Details: |
|
ISBN-13: |
978-3-8433-6219-1 |
ISBN-10: |
384336219X |
EAN: |
9783843362191 |
Book language: |
English |
By (author) : |
Genevieve Etornam Adukpo |
Number of pages: |
112 |
Published on: |
2010-10-14 |
Category: |
Organic chemistry |