scholarly journals Regio- and Diastereoselective Synthesis of 2-Arylazetidines: Quantum Chemical Explanation of Baldwin’s Rules for the Ring-Formation Reactions of Oxiranes

2020 ◽  
Vol 85 (17) ◽  
pp. 11226-11239
Author(s):  
Ervin Kovács ◽  
Ferenc Faigl ◽  
Zoltán Mucsi
Keyword(s):  
Quantum Chemical ◽  
Ring Formation ◽  
Diastereoselective Synthesis

Diastereoselective Synthesis of (3R,5R)-γ-Hydroxypiperazic Acid

Synlett ◽  
2021 ◽  
Author(s):  
Juan R. Del Valle ◽  
Taylor A. Gerrein ◽  
Yassin M. Elbatrawi
Keyword(s):  
Asymmetric Synthesis ◽  
Late Stage ◽  
Ring Formation ◽  
Peptide Chain ◽  
Nonribosomal Peptides ◽  
Diastereoselective Synthesis ◽  
Hydroxylation Reaction ◽  
Enolate Hydroxylation

AbstractWe report an asymmetric synthesis of the (3R,5R)-γ-hydroxypiperazic acid (γ-OHPiz) residue encountered in several bioactive nonribosomal peptides. Our strategy relies on a diastereoselective enolate hydroxylation reaction and electrophilic N-amination to provide the acyclic γ-OHPiz precursor. This orthogonally protected α-hydrazino acid intermediate is amenable to late-stage diazinane ring formation following incorporation into a peptide chain. We determined the N-terminal amide rotamer propensity of the γ-OHPiz residue and showed that the γ-OH substituent enhances trans-amide bias relative to piperazic acid.

Butenolide ring formation in cardenolide biosynthesis: Spontaneous cyclization of pregnane-21-O-malonyl hemiesters

Planta Medica ◽  
2007 ◽  
Vol 73 (09) ◽  
Author(s):  
RM Pádua ◽  
R Waibel ◽  
SP Kuate ◽  
PK Riedl ◽  
P Gmeiner ◽  
...  
Keyword(s):  
Ring Formation

Quantum Chemical Studies of Hole Transfer in Liquid Hexane

2017 ◽  
Vol 137 (7) ◽  
pp. 435-441
Author(s):  
Masahiro Sato ◽  
Akiko Kumada ◽  
Kunihiko Hidaka ◽  
Toshiyuki Hirano ◽  
Fumitoshi Sato
Keyword(s):  
Quantum Chemical ◽  
Hole Transfer ◽  
Chemical Studies ◽  
Quantum Chemical Studies

Examination on Permittivity Estimation of Hydrocarbon-based Thermosetting Resin based on Quantum Chemical Calculation

2017 ◽  
Vol 137 (11) ◽  
pp. 626-631 ◽  
Author(s):  
Yuki Fuchi ◽  
Ryota Nakasako ◽  
Masahiro Kozako ◽  
Masayuki Hikita ◽  
Nobuhito Kamei
Keyword(s):  
Quantum Chemical Calculation ◽  
Quantum Chemical ◽  
Chemical Calculation ◽  
Thermosetting Resin
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