Abstract
In order to achieve the diastereo-differentiation of π-faces, we have developed the protected vicinal-diol controller. The striking successes in stereocontrol of diverse organic reactions have been recorded for which the diastereofacial bias constructed by such diol controller should be responsible. We refer to this topological situation as "outside-inside bias". This review summarizes the application of this concept to nitrone-olefin [3+2] cycloaddition reactions which resulted in considerable successes in stereocontrol again, and covers three topics, (1) the substrate-controlled intermolecular asymmetric cycloaddition reactions, (2) intramolecular 1,3-dipolar cycloaddition reactions of chiral alkenylnitrones, and (3) the synthesis of cyclic chiral nitrones and its intermolecular asymmetric cycloaddition reactions with various olefins. The role of the vicinal diol controller in these processes has been delineated.
| Original language | English |
|---|---|
| Pages (from-to) | 86-95 |
| Number of pages | 10 |
| Journal | Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry |
| Volume | 56 |
| Issue number | 2 |
| Publication status | Published - Feb 1998 |
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Keywords
- Alkenyl nitrones
- Cyclic chiral nitrone
- Diastereofacial bias
- Diastereoselection
- Intermolecular asymmetric cycloaddition reaction
- Intramolecular asymmetric cycloaddition reaction
- Nitrone-olefin [3+2] cycloaddition
- Vicinal diol controller
ASJC Scopus subject areas
- Organic Chemistry
Cite this
Asymmetric bias generated by protected vicinal diol controller and its application to asymmetric nitrone-olefin cycloaddition reactions. / Saito, Seiki; Ishikawa, Teruhiko.
In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Vol. 56, No. 2, 02.1998, p. 86-95.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Asymmetric bias generated by protected vicinal diol controller and its application to asymmetric nitrone-olefin cycloaddition reactions
AU - Saito, Seiki
AU - Ishikawa, Teruhiko
PY - 1998/2
Y1 - 1998/2
N2 - In order to achieve the diastereo-differentiation of π-faces, we have developed the protected vicinal-diol controller. The striking successes in stereocontrol of diverse organic reactions have been recorded for which the diastereofacial bias constructed by such diol controller should be responsible. We refer to this topological situation as "outside-inside bias". This review summarizes the application of this concept to nitrone-olefin [3+2] cycloaddition reactions which resulted in considerable successes in stereocontrol again, and covers three topics, (1) the substrate-controlled intermolecular asymmetric cycloaddition reactions, (2) intramolecular 1,3-dipolar cycloaddition reactions of chiral alkenylnitrones, and (3) the synthesis of cyclic chiral nitrones and its intermolecular asymmetric cycloaddition reactions with various olefins. The role of the vicinal diol controller in these processes has been delineated.
AB - In order to achieve the diastereo-differentiation of π-faces, we have developed the protected vicinal-diol controller. The striking successes in stereocontrol of diverse organic reactions have been recorded for which the diastereofacial bias constructed by such diol controller should be responsible. We refer to this topological situation as "outside-inside bias". This review summarizes the application of this concept to nitrone-olefin [3+2] cycloaddition reactions which resulted in considerable successes in stereocontrol again, and covers three topics, (1) the substrate-controlled intermolecular asymmetric cycloaddition reactions, (2) intramolecular 1,3-dipolar cycloaddition reactions of chiral alkenylnitrones, and (3) the synthesis of cyclic chiral nitrones and its intermolecular asymmetric cycloaddition reactions with various olefins. The role of the vicinal diol controller in these processes has been delineated.
KW - Alkenyl nitrones
KW - Cyclic chiral nitrone
KW - Diastereofacial bias
KW - Diastereoselection
KW - Intermolecular asymmetric cycloaddition reaction
KW - Intramolecular asymmetric cycloaddition reaction
KW - Nitrone-olefin [3+2] cycloaddition
KW - Vicinal diol controller
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UR - http://www.scopus.com/inward/citedby.url?scp=18944380400&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:18944380400
VL - 56
SP - 86
EP - 95
JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
SN - 0037-9980
IS - 2
ER -