75581-01-0Relevant articles and documents
Catalytic Asymmetric Synthesis of Unprotected β2-Amino Acids
Zhu, Chendan,Mandrelli, Francesca,Zhou, Hui,Maji, Rajat,List, Benjamin
supporting information, p. 3312 - 3317 (2021/04/07)
We report here a scalable, catalytic one-pot approach to enantiopure and unmodified β2-amino acids. A newly developed confined imidodiphosphorimidate (IDPi) catalyzes a broadly applicable reaction of diverse bis-silyl ketene acetals with a silylated aminomethyl ether, followed by hydrolytic workup, to give free β2-amino acids in high yields, purity, and enantioselectivity. Importantly, both aromatic and aliphatic β2-amino acids can be obtained using this method. Mechanistic studies are consistent with the aminomethylation to proceed via silylium-based asymmetric counteranion-directed catalysis (Si-ACDC) and a transition state to explain the enantioselectivity is suggested on the basis of density functional theory calculation.
Synthesis of 7,8-benzo-9-aza-4-oxabicyclo[3.3.1]nonan-3-ones by sequential 'condensation-iodolactonization' reactions of 1,1-bis(trimethylsilyloxy)ketene acetals with isoquinolines
Ullah, Ehsan,Rotzoll, Sven,Schmidt, Andreas,Michalik, Dirk,Langer, Peter
, p. 8997 - 8999 (2007/10/03)
Functionalized 7,8-benzo-9-aza-4-oxabicyclo[3.3.1]nonan-3-ones were prepared by regio- and diastereoselective condensation of 1,1-bis(silyloxy) ketene acetals with isoquinolinium salts and subsequent regioselective and stereospecific iodolactonization.
α-Fluorination of Carbonyl Compounds with CF3OF
Middleton, W. J.,Bingham, E. M.
, p. 4845 - 4846 (2007/10/02)
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