204587-97-3Relevant articles and documents
Trading N and O. Part 3: Synthesis of 1,2,3,4-tetrahydroisoquinolines from α-hydroxy-β-amino esters
Davies, Stephen G.,Fletcher, Ai M.,Frost, Aileen B.,Kennedy, Matthew S.,Roberts, Paul M.,Thomson, James E.
, p. 2139 - 2163 (2016/04/09)
A range of enantiopure 1,2,3,4-tetrahydroisoquinolines have been prepared directly from α-hydroxy-β-amino esters. Activation of the α-hydroxy group upon treatment with Tf2O and 2,6-di-tert-butyl-4-methylpyridine promotes aziridinium formation,
A new method for deprotection of benzothiazolesulfonamides using a thiol and base
Wuts, Peter G. M.,Gu, Rui Lin,Northuis, Jill M.,Thomas, Collette L.
, p. 9155 - 9156 (2007/10/03)
Benzothiazolesulfonamides of primary and secondary amines are efficiently cleaved by a nucleophilic aromatic substitution with a thiol and a base such as potassium t-butoxide or diisopropylethyl amine in DMF.
Asymmetric Synthesis of β-Amino-α-Hydroxy Acids via Diastereoselective Hydroxylation of Homochiral β-Amino Enolates
Bunnage, Mark E.,Chernega, Alexander N.,Davies, Stephen G.,Goodwin, Christopher J.
, p. 2373 - 2384 (2007/10/02)
The highly diastereoselective conjugate addition of lithium N-benzyl-N-α-methylbenzylamide with enoate acceptors, and the electrophilic hydroxylation of the resultant β-amino enolates with (camphorsulfonyl)oxaziridine, is identified as a direct and general strategy for the asymmetric synthesis of homochiral β-amino-α-hydroxy acids and their derivatives.A structurally diverse array of β-amino enolate substrates can be hydroxylated with generally excellent anti diastereoselectivity (>90percent d.e.) using this protocol; an alternative stepwise hydroxylation procedure, where the β-amino enolate is prepared by enolisation of the preformed conjugate adduct is also found to lead to formation of the anti diastereomer.The diastereofacial selectivity of enolate hydroxylation appears to be under predominantly substrate-controlled asymmetric induction, although a measurable degree of chirality predominantly substrate-controlled asymmetric induction, although a measurable degree of chirality recognition with the oxaziridine reagent can be observed.Homochiral β-amino-α-keto esters are also prepared and their stereoselective reductions examined.
