Abstract
The development of asymmetric 1,2-additions of organometallics to carbonyl compounds and imines for the synthesis of chiral alcohols and amines has been overviewed. The highly enantioselective addition reactions of dialkylzincs to aldehydes developed in the mid-1980s have definitely played a key role in this field of chemistry. Hundreds of chiral sources which promote additions of zinc alkyl groups to aldehydes with high enantioselectivities have appeared in the literature, and the chemistry became one of the milestones of asymmetric catalysis in organic synthesis. The subsequent progress in the efficient catalytic asymmetric synthesis of tertiary alcohols by the reactions of ketones and organometallic reagents is also outstanding. Over the past decade, catalytic enantioselective synthesis of chiral amines using asymmetric 1,2-addition of organometallics to imines has become a matter of common knowledge.
| Original language | English |
|---|---|
| Title of host publication | Comprehensive Chirality |
| Publisher | Elsevier Ltd |
| Pages | 328-342 |
| Number of pages | 15 |
| Volume | 4 |
| ISBN (Print) | 9780080951683 |
| DOIs | |
| Publication status | Published - Sep 2012 |
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Keywords
- Aldehyde
- Chiral alcohol
- Chiral amine
- Enantioselective addition
- Grignard reagent
- Imine
- Ketone
- Organolithium
- Organomagnesium
- Organozinc
ASJC Scopus subject areas
- Chemistry(all)
Cite this
4.17 Asymmetric 1,2-Addition of Organometallics to Carbonyl and Imine Groups. / Suga, Seiji; Kitamura, M.
Comprehensive Chirality. Vol. 4 Elsevier Ltd, 2012. p. 328-342.Research output: Chapter in Book/Report/Conference proceeding › Chapter
}
TY - CHAP
T1 - 4.17 Asymmetric 1,2-Addition of Organometallics to Carbonyl and Imine Groups
AU - Suga, Seiji
AU - Kitamura, M.
PY - 2012/9
Y1 - 2012/9
N2 - The development of asymmetric 1,2-additions of organometallics to carbonyl compounds and imines for the synthesis of chiral alcohols and amines has been overviewed. The highly enantioselective addition reactions of dialkylzincs to aldehydes developed in the mid-1980s have definitely played a key role in this field of chemistry. Hundreds of chiral sources which promote additions of zinc alkyl groups to aldehydes with high enantioselectivities have appeared in the literature, and the chemistry became one of the milestones of asymmetric catalysis in organic synthesis. The subsequent progress in the efficient catalytic asymmetric synthesis of tertiary alcohols by the reactions of ketones and organometallic reagents is also outstanding. Over the past decade, catalytic enantioselective synthesis of chiral amines using asymmetric 1,2-addition of organometallics to imines has become a matter of common knowledge.
AB - The development of asymmetric 1,2-additions of organometallics to carbonyl compounds and imines for the synthesis of chiral alcohols and amines has been overviewed. The highly enantioselective addition reactions of dialkylzincs to aldehydes developed in the mid-1980s have definitely played a key role in this field of chemistry. Hundreds of chiral sources which promote additions of zinc alkyl groups to aldehydes with high enantioselectivities have appeared in the literature, and the chemistry became one of the milestones of asymmetric catalysis in organic synthesis. The subsequent progress in the efficient catalytic asymmetric synthesis of tertiary alcohols by the reactions of ketones and organometallic reagents is also outstanding. Over the past decade, catalytic enantioselective synthesis of chiral amines using asymmetric 1,2-addition of organometallics to imines has become a matter of common knowledge.
KW - Aldehyde
KW - Chiral alcohol
KW - Chiral amine
KW - Enantioselective addition
KW - Grignard reagent
KW - Imine
KW - Ketone
KW - Organolithium
KW - Organomagnesium
KW - Organozinc
UR - http://www.scopus.com/inward/record.url?scp=84887096674&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84887096674&partnerID=8YFLogxK
U2 - 10.1016/B978-0-08-095167-6.00416-X
DO - 10.1016/B978-0-08-095167-6.00416-X
M3 - Chapter
AN - SCOPUS:84887096674
SN - 9780080951683
VL - 4
SP - 328
EP - 342
BT - Comprehensive Chirality
PB - Elsevier Ltd
ER -