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Diastereoselective Synthesis of Spiro-β-lactams via Staudinger Reaction.

✍ Scribed by Susana Rojas-Lima; Lidia Santillan-Sid; Heraclio Lopez-Ruiz; Alejandro Alvarez-Hernandez

Publisher
John Wiley and Sons
Year
2007
Weight
24 KB
Volume
38
Category
Article
ISSN
0931-7597

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Diastereoselective Synthesis of Highly C
Diastereoselective Synthesis of Highly Constrained Spiro-β-Lactams by the Staudinger Reaction Using an Unsymmetrical Bicyclic Ketene
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## Abstract A rigid bicyclic ketene was used to generate highly constrained polycyclic spiro‐β‐lactams through the Staudinger reaction. Depending on the imine component, high diastereoselectivity was observed in the process, leading to mainly the __cis__ diastereoisomer in the case of aromatic imin

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2 + 2] Cycloaddition reactions between ketenes, bearing known. In this way β-lactams with a widely varying substitution pattern at the C-3 and C-4 positions of the ring amino-, oxy-, or halo-groups, and imines are recognized as being amongst the most important and direct routes to β-are constructed