An Efficient Petasis Boronic-Mannich Reaction of Chiral Lactol Derivatives Prepared from D-Araboascorbic Acid

被引：8

作者：

Mandai, Hiroki ^{[1
]}

Yamada, Hiroshi ^{[1
]}

Shimowaki, Keita ^{[1
]}

Mitsudo, Koichi ^{[1
]}

Suga, Seiji ^{[1
,2
,3
]}

机构：

[1] Okayama Univ, Grad Sch Nat Sci & Technol, Div Chem & Biotechnol, Kita Ku, Okayama 7008530, Japan

[2] Okayama Univ, Res Ctr New Funct Mat Energy Prod Storage & Trans, Kita Ku, Okayama 7008530, Japan

[3] Japan Sci & Technol Agcy, ACT C, Kawaguchi, Saitama 3320012, Japan

来源：

SYNTHESIS-STUTTGART | 2014年 / 46卷 / 19期

关键词：

asymmetric synthesis; chiral pool; coupling; diastereoselectivity; domino reaction; lactones; ALPHA-HYDROXY ALDEHYDES; ASYMMETRIC MULTICOMPONENT REACTIONS; 3,4-DIEPIPOLYOXAMIC ACID; 3-COMPONENT REACTION; (-)-POLYOXAMIC ACID; ORGANOBORONIC ACIDS; FORMAL SYNTHESIS; AMINO-ALCOHOLS; CONDENSATION; ENANTIOMERS;

D O I：

10.1055/s-0034-1378900

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2672 / 2681

页数：10

共 3 条

[1] Asymmetry in the boronic acid Mannich reaction: Diastereocontrolled addition to chiral iminium species derived from aldehydes and (S)-5-phenylmorpholin-2-one
Harwood, LM
Currie, GS
Drew, MGB
Luke, RWA
CHEMICAL COMMUNICATIONS, 1996, (16) : 1953 - 1954
[2] An efficient method for preparation of chiral macrocyclic bisamides starting from diol derivatives of D-mannitol and L-tartaric acid
Gryko, DT
Piatek, P
Jurczak, J
SYNTHESIS-STUTTGART, 1999, (02): : 336 - 340
[3] A novel and efficient route to (E)-alk-1-enyl boronic acid derivatives from (E)-1-(trimethylsilyl)alk-1-enes and a formal Suzuki-Miyaura cross-coupling reaction starting with vinylsilanes
Farinola, GM
Fiandanese, V
Mazzone, L
Naso, F
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (24) : 2523 - 2524

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