DIASTEREOSELECTIVE REDUCTION OF CHIRAL N-TOSYL-2-BENZOYL-1,3-OXAZINE DERIVED FROM (1R)-(+)-CAMPHOR

被引：2

作者：

Ko, Kwang-Youn ^{[1
]}

Yun, Hoseop ^{[2
]}

机构：

[1] Ajou Univ, Dept Chem, Suwon 443749, South Korea

[2] Ajou Univ, Div Energy Syst Res, Suwon 443749, South Korea

来源：

HETEROCYCLES | 2010年 / 81卷 / 10期

关键词：

Reduction; Diastereoselectivity; 1,3-Oxazine; Chelate Model; (+)-Camphor; GLYCOLS RCHOHCH2OH; D-GLUCOSE; ADDITIONS; AUXILIARY; PURITY;

D O I：

10.3987/COM-10-12016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereochemistry of reduction of chiral N-tosyl-2-benzoyl-1,3-oxazine prepared by condensation of 1,3-amino alcohol derived from (1R)-(+)-camphor with phenylglyoxal was investigated using various reducing agents. Based on X-ray crystallography, 2-benzoyl group in 1,3-oxazine ring was situated in the axial position. High diastereoselectivity observed in the hydride reduction can be explained by a chelate model where N-tosyl oxygen atom takes part in chelation rather than ring oxygen atom.

引用

页码：2351 / 2359

页数：9

共 7 条

[1] Diastereoselective Reduction of Chiral 2-(1-Alkenoyl)- and 2-(1-Alkynoyl)-1,3-Oxathiane 3-Oxides Derived from (1R)-(+)-Camphor
Ko, Kwang-Youn
Yun, Hoseop
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (07) : 2415 - 2418
[2] Stereoselective Syntheses of (+)-Broussonetine D and (+)-Australine via a Functionalized Pyrrolidine from an Extended Chiral 1,3-Oxazine
Myeong, In-Soo
Ham, Won-Hun
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (05) : 1077 - 1082
[3] SYNTHESIS OF CHIRAL 1,5-DIAMINES DERIVED FROM (R)-(+)-CAMPHOR
Martins, Jose E. D.
Kray, Luciana J.
dos Santos, Greice M.
QUIMICA NOVA, 2024,
[4] Diastereoselective reduction of 2-acyl-1,3-dioxanes derived from D-glucose
Ko, KY
Park, JY
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2002, 23 (05) : 665 - 666
[5] Synthesis and stereoselective evaluation of a (1R)-(-)-myrtenal-derived pseudo C2-symmetric dodecaheterocycle as a potential heterofunctional chiral auxiliary
Sanchez-Chavez, Anahi C.
Elena Vargas-Diaz, Ma.
Ontiveros-Rodriguez, Julio C.
Perez-Estrada, Salvador
Flores-Bernal, Gustavo G.
Mendoza-Espinosa, Daniel
Alvarez-Hernandez, Alejandro
Delgado, Francisco
Tamariz, Joaquin
Gerardo Zepeda-Vallejo, L.
TETRAHEDRON LETTERS, 2018, 59 (50) : 4437 - 4441
[6] Asymmetric induction in the 1,3-dipolar cycloaddition of chiral nitrile oxide derived from (2R)-bornane-10,2-sultam
Józwik, J
Kosior, M
Kiegiel, J
Jurczak, J
CHIRALITY, 2001, 13 (10) : 629 - 630
[7] Diastereoselective reaction of (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3- propanediol with aromatic aldehydes. Synthesis of (1R,2R,4S,5S,8S)-2,8-diaryl-4- (4-nitrophenyl)-1-aza-3,7-dioxabicyclo[3.3.0]octanes
Madesclaire M.
Coudert P.
Gaumet V.
Zaitsev V.P.
Zaitseva Yu.V.
Chemistry of Heterocyclic Compounds, 2006, 42 (5) : 665 - 670

← 1 →