Abstract
Optically active polyhydroxy trans-1,2-amino alcohols were efficiently synthesized in good to excellent yields by the Petasis boronic-Mannich reaction of an amine, an organoboronic acid, and a chiral lactol, which was prepared from d-araboascorbic acid or its diastereomer. Further transformations of the resulting Petasis products were investigated in detail to obtain chiral building blocks containing three continuous stereogenic centers.
| Original language | English |
|---|---|
| Article number | ss-2014-c0373-op |
| Pages (from-to) | 2672-2681 |
| Number of pages | 10 |
| Journal | Synthesis |
| Volume | 46 |
| Issue number | 19 |
| DOIs | |
| Publication status | Published - Oct 1 2014 |
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Keywords
- asymmetric synthesis
- chiral pool
- coupling
- diastereoselectivity
- domino reaction
- lactones
ASJC Scopus subject areas
- Organic Chemistry
- Catalysis
Cite this
An Efficient Petasis Boronic-Mannich Reaction of Chiral Lactol Derivatives Prepared from d -Araboascorbic Acid. / Mandai, Hiroki; Yamada, Hiroshi; Shimowaki, Keita; Mitsudo, Koichi; Suga, Seiji.
In: Synthesis, Vol. 46, No. 19, ss-2014-c0373-op, 01.10.2014, p. 2672-2681.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - An Efficient Petasis Boronic-Mannich Reaction of Chiral Lactol Derivatives Prepared from d -Araboascorbic Acid
AU - Mandai, Hiroki
AU - Yamada, Hiroshi
AU - Shimowaki, Keita
AU - Mitsudo, Koichi
AU - Suga, Seiji
PY - 2014/10/1
Y1 - 2014/10/1
N2 - Optically active polyhydroxy trans-1,2-amino alcohols were efficiently synthesized in good to excellent yields by the Petasis boronic-Mannich reaction of an amine, an organoboronic acid, and a chiral lactol, which was prepared from d-araboascorbic acid or its diastereomer. Further transformations of the resulting Petasis products were investigated in detail to obtain chiral building blocks containing three continuous stereogenic centers.
AB - Optically active polyhydroxy trans-1,2-amino alcohols were efficiently synthesized in good to excellent yields by the Petasis boronic-Mannich reaction of an amine, an organoboronic acid, and a chiral lactol, which was prepared from d-araboascorbic acid or its diastereomer. Further transformations of the resulting Petasis products were investigated in detail to obtain chiral building blocks containing three continuous stereogenic centers.
KW - asymmetric synthesis
KW - chiral pool
KW - coupling
KW - diastereoselectivity
KW - domino reaction
KW - lactones
UR - http://www.scopus.com/inward/record.url?scp=84923373000&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84923373000&partnerID=8YFLogxK
U2 - 10.1055/s-0034-1378900
DO - 10.1055/s-0034-1378900
M3 - Article
AN - SCOPUS:84923373000
VL - 46
SP - 2672
EP - 2681
JO - Synthesis
JF - Synthesis
SN - 0039-7881
IS - 19
M1 - ss-2014-c0373-op
ER -