Synthesis of Novel,Chiral Bicyclo[3.1.0]hex‐2‐ene Amino Acid Derivatives as Useful Synthons in Medicinal Chemistry |
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Authors: | Heinz Stadler |
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Institution: | Roche Pharma Research and Early Development, Small Molecule Research, Roche Innovation Center Basel, F. Hoffmann‐La Roche Ltd., Picassoplatz, Lautengartenstrasse 6, CH‐4070 Basel, (phone: +41‐62‐6875752) |
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Abstract: | A short and concise synthesis of novel, chiral bicyclo3.1.0]hex‐2‐ene amino acid derivatives 13 and 14 has been developed. The key step is a stereo‐ and regioselective allylic amination of exo‐ and endo‐methyl bicyclo3.1.0]hex‐2‐ene‐6‐carboxylates 8 and 9 , which were prepared from 7,7‐dichlorobicyclo3.2.0]hept‐2‐en‐6‐one ( 1 ). These amino acid derivatives are useful building blocks in medicinal chemistry and can be prepared as chiral compounds by using either (+)‐ 1 or (?)‐ 1 as starting material. |
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Keywords: | Allylic amination Bicyclo[3 1 0]hex‐2‐ene amino acid Glycines (2‐Carboxycyclopropyl)‐ Fsp3‐Rich building blocks |
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