Garner¿s aldehyde
An important chiral ¿- amino aldehyde in organic chemistry
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Chiral amino aldehydes are remarkable, as their aldehyde groups can be converted into a wide range of structural frameworks are the intermediates in several important industrial processes. However, the characteristic reactivity of amine and aldehyde functionalities is a major task in case of preparation and synthetic efficacy of -amino aldehydes as nitrogen protection assists undesired epimerization processes. Fischer's discovery of glucosamine in 1902 in which unprotected amine and aldehyde functionalities are stabilized as a cyclic hemiacetal is the first example of unprotected -amino aldehy...
Chiral amino aldehydes are remarkable, as their aldehyde groups can be converted into a wide range of structural frameworks are the intermediates in several important industrial processes. However, the characteristic reactivity of amine and aldehyde functionalities is a major task in case of preparation and synthetic efficacy of -amino aldehydes as nitrogen protection assists undesired epimerization processes. Fischer's discovery of glucosamine in 1902 in which unprotected amine and aldehyde functionalities are stabilized as a cyclic hemiacetal is the first example of unprotected -amino aldehydes. Later on, he also synthesized glycinal, which was characterized through degradation studies due to its inherent instability via self-condensation. The probability for intramolecular stabilization of -amino aldehydes is not significant but the presence of incompatible functional groups make these unstable and hence, suitable N-and C-protection is vital.
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