@article { ISI:000350222400046, title = {One-pot highly enantio- and diastereoselective synthesis of anti,anti vinylic 3-amino-1,2 diols via proline catalyzed sequential alpha-amination/benzoyloxyallylation of aldehydes}, journal = {RSC Advances}, volume = {5}, number = {28}, year = {2015}, month = {FEB}, pages = {21803-21805}, publisher = {ROYAL SOC CHEMISTRY}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

The first direct asymmetric synthesis of anti, anti vinylic 3-amino-1,2-diols from aldehydes is described via a one-pot sequential L-proline catalyzed alpha-amination/benzoyloxyallylation protocol. The reaction proceeds with exceptionally high diastereoselectivity (\>99\%) as can be explained based on the Felkin-Ahn transition state model. Its effectiveness is proven unambiguously by demonstrating a short asymmetric synthesis of D-ribo-phytosphingosine tetraacetate (93\% ee).

}, issn = {2046-2069}, doi = {10.1039/c5ra02830b}, author = {Ahuja, Brij Bhushan and Sudalai, Arumugam} } @inbook {47308, title = {Organocatalyzed α-aminooxylation/amination of aldehydes and their sequential reactions: a versatile tool for the synthesis of bioactive molecules}, booktitle = {Bioactive Natural Products}, volume = {64}, year = {2020}, pages = {417-465}, publisher = {Elsevier B.V.}, organization = {Elsevier B.V.}, abstract = {

This chapter introduces the sequential reactions of proline catalyzed α-aminooxylation and α-amination of aldehydes and its broad applications in the synthesis of bioactive molecules. It starts by presenting an overview of organocatalysis, particularly proline and its catalytic behavior. It then explains the proline catalyzed α-aminooxylation reaction and its sequential reactions one by one along with its applications in the synthesis of natural products. Next, it describes the\ l- and\ d-proline catalyzed α-amination and its sequential reactions. A full description of the synthetic scheme of natural products is provided.

}, doi = {10.1016/B978-0-12-817903-1.00014-0}, author = {Ahuja, Brij Bhushan and Sudalai, Arumugum} }