@article {47097,
	title = {Divergent approach to the synthesis of (-)-balanol heterocycle and cis-3-hydroxypipecolic acid based on chiral 2-aminoalkanol equivalent},
	journal = {Tetrahedron},
	volume = {80},
	year = {2021},
	month = {JAN},
	pages = {131773},
	type = {Article},
	abstract = {<p>Enantioselective synthesis of the hexahydroazepine core of (-)-balanol and formal synthesis of cis-3hydroxypipecolic acid from a common intermediate have been accomplished by a divergent path. The common intermediate was accessed from a favorably protected enantiomerically pure 2-amino-1,3,4-butanetriol (ABT) equivalent via oxidation and Wittig olefination. The synthesis of (-)-balanol heterocycle featured tandem reduction/acetal-deprotection/gamma-lactonization reaction and a one-pot azide reduction followed by seven membered aza-heterocycle formation while the route to cis-3-hydroxypipecolic acid highlighted the base induced piperidine ring formation and regioselective benzylidine-acetal cleavage. (C) 2020 Elsevier Ltd. All rights reserved.</p>
},
	keywords = {Amino-alcohol, desymmetrization, Hexahydroazepine, Piperidine alkaloids, Protein kinase},
	issn = {0040-4020},
	doi = {10.1016/j.tet.2020.131773},
	author = {Chavan, Subhash P. and Kalbhor, Dinesh B. and Gonnade, Rajesh G.}
}
@article {47386,
	title = {NHC-catalyzed desymmetrization of N-aryl maleimides leading to the atroposelective synthesis of N-Aryl succinimides},
	journal = {Angewandte Chemie-International Edition},
	volume = {60},
	year = {2021},
	month = {MAY },
	pages = {12264-12268},
	type = {Article},
	abstract = {<p>Although the construction of axially chiral C-C bonds leading to the atroposelective synthesis of biaryls and allied compounds are well-known, the related synthesis of compounds bearing axially chiral C-N bonds are relatively rare. Described herein is the N-heterocyclic carbene-catalyzed atroposelective synthesis of N-aryl succinimides having an axially chiral C-N bond via the desymmetrization of N-aryl maleimides. The NHC involved intermolecular Stetter-aldol cascade of dialdehydes with prochiral N-aryl maleimides followed by oxidation afforded N-aryl succinimides in good yields and ee values. Preliminary studies on rotation barrier for the C-N bond, the temperature dependence, and detailed DFT studies on mechanism are also provided.</p>},
	keywords = {asymmetric catalysis, axial chirality, desymmetrization, N-heterocyclic carbenes, organocatalysis},
	issn = {1433-7851},
	doi = {10.1002/anie.202016938, Early Access Date = APR 2021},
	author = {Barik, Soumen and Shee, Sayan and Das, Soumik and Gonnade, Rajesh G. and Jindal, Garima and Mukherjee, Subrata and Biju, Akkattu T.}
}
