Enantioselective Synthesis of Optically Active Pyridine Derivatives and C 2 ‐Symmetric 2,2′‐Bipyridines
Optically active pyridine derivatives 2, 15, 18, 19, 21, 26 , and 27 are obtained by enantioselective reduction of the corresponding ketones 5, 7, 11–13, 24 , and 25 using the chiral borane reagent chlorodiisopinocampheylborane [(I pc ) 2 BCl]. Nickel(0)‐mediated coupling of bromopyridines 2, 15 , a...
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| Veröffentlicht in: | Chemische Berichte 1992-05, Vol.125 (5), p.1169-1190 |
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| container_title | Chemische Berichte |
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| creator | Bolm, Carsten Ewald, Martina Felder, Marcel Schlingloff, Gunther |
| description | Optically active pyridine derivatives
2, 15, 18, 19, 21, 26
, and
27
are obtained by enantioselective reduction of the corresponding ketones
5, 7, 11–13, 24
, and
25
using the chiral borane reagent chlorodiisopinocampheylborane [(I
pc
)
2
BCl]. Nickel(0)‐mediated coupling of bromopyridines
2, 15
, and
31
gives
C
2
‐symmetric 2,2′‐bipyridines (
R,R
)‐
32
, (
R,R′
)‐
33
, and (
S,S
)‐
38
, respectively, which form metal complexes with Co
II
, Pd
II
, Cu
I
, and Ag
I
. Aryl‐substituted pyridines
26
, and
39–41
are synthesized by palladium(0)‐catalyzed cross couplings of
2
and
15
with boronic acids
42–44
. |
| doi_str_mv | 10.1002/cber.19921250528 |
| format | Article |
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2, 15, 18, 19, 21, 26
, and
27
are obtained by enantioselective reduction of the corresponding ketones
5, 7, 11–13, 24
, and
25
using the chiral borane reagent chlorodiisopinocampheylborane [(I
pc
)
2
BCl]. Nickel(0)‐mediated coupling of bromopyridines
2, 15
, and
31
gives
C
2
‐symmetric 2,2′‐bipyridines (
R,R
)‐
32
, (
R,R′
)‐
33
, and (
S,S
)‐
38
, respectively, which form metal complexes with Co
II
, Pd
II
, Cu
I
, and Ag
I
. Aryl‐substituted pyridines
26
, and
39–41
are synthesized by palladium(0)‐catalyzed cross couplings of
2
and
15
with boronic acids
42–44
.</description><identifier>ISSN: 0009-2940</identifier><identifier>DOI: 10.1002/cber.19921250528</identifier><language>eng</language><ispartof>Chemische Berichte, 1992-05, Vol.125 (5), p.1169-1190</ispartof><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c888-365c2fa36318413db478729308e54ff7402756d1ca32ec0d12d1c71c058068eb3</citedby><cites>FETCH-LOGICAL-c888-365c2fa36318413db478729308e54ff7402756d1ca32ec0d12d1c71c058068eb3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Bolm, Carsten</creatorcontrib><creatorcontrib>Ewald, Martina</creatorcontrib><creatorcontrib>Felder, Marcel</creatorcontrib><creatorcontrib>Schlingloff, Gunther</creatorcontrib><title>Enantioselective Synthesis of Optically Active Pyridine Derivatives and C 2 ‐Symmetric 2,2′‐Bipyridines</title><title>Chemische Berichte</title><description>Optically active pyridine derivatives
2, 15, 18, 19, 21, 26
, and
27
are obtained by enantioselective reduction of the corresponding ketones
5, 7, 11–13, 24
, and
25
using the chiral borane reagent chlorodiisopinocampheylborane [(I
pc
)
2
BCl]. Nickel(0)‐mediated coupling of bromopyridines
2, 15
, and
31
gives
C
2
‐symmetric 2,2′‐bipyridines (
R,R
)‐
32
, (
R,R′
)‐
33
, and (
S,S
)‐
38
, respectively, which form metal complexes with Co
II
, Pd
II
, Cu
I
, and Ag
I
. Aryl‐substituted pyridines
26
, and
39–41
are synthesized by palladium(0)‐catalyzed cross couplings of
2
and
15
with boronic acids
42–44
.</description><issn>0009-2940</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1992</creationdate><recordtype>article</recordtype><recordid>eNpNkEtOwzAYhL0AiVLYs_QBSPn9Ow9nWUJ5SJWK1O4jx_kjjPKSHVXKrkfgLBypJ6FRu2A1oxnNLD7GHgQsBAA-mYLcQqQpCowgQnXFZgCQBpiGcMNuvf8GkGESyxlrVq1uB9t5qskMdk98O7bDF3nreVfxTT9Yo-t65Mtz-zk6W9qW-As5u9dT5rluS55x5MfDz3ZsGhqcNRwf8Xj4PUXPtr-M_B27rnTt6f6ic7Z7Xe2y92C9efvIluvAKKUCGUcGKy1jKVQoZFmEiUowlaAoCqsqCQGTKC6F0RLJQCnw5BNhIFIQKyrknMH51rjOe0dV3jvbaDfmAvKJUD4Ryv8Rkn8G-l8Z</recordid><startdate>199205</startdate><enddate>199205</enddate><creator>Bolm, Carsten</creator><creator>Ewald, Martina</creator><creator>Felder, Marcel</creator><creator>Schlingloff, Gunther</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>199205</creationdate><title>Enantioselective Synthesis of Optically Active Pyridine Derivatives and C 2 ‐Symmetric 2,2′‐Bipyridines</title><author>Bolm, Carsten ; Ewald, Martina ; Felder, Marcel ; Schlingloff, Gunther</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c888-365c2fa36318413db478729308e54ff7402756d1ca32ec0d12d1c71c058068eb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1992</creationdate><toplevel>online_resources</toplevel><creatorcontrib>Bolm, Carsten</creatorcontrib><creatorcontrib>Ewald, Martina</creatorcontrib><creatorcontrib>Felder, Marcel</creatorcontrib><creatorcontrib>Schlingloff, Gunther</creatorcontrib><collection>CrossRef</collection><jtitle>Chemische Berichte</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bolm, Carsten</au><au>Ewald, Martina</au><au>Felder, Marcel</au><au>Schlingloff, Gunther</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Synthesis of Optically Active Pyridine Derivatives and C 2 ‐Symmetric 2,2′‐Bipyridines</atitle><jtitle>Chemische Berichte</jtitle><date>1992-05</date><risdate>1992</risdate><volume>125</volume><issue>5</issue><spage>1169</spage><epage>1190</epage><pages>1169-1190</pages><issn>0009-2940</issn><abstract>Optically active pyridine derivatives
2, 15, 18, 19, 21, 26
, and
27
are obtained by enantioselective reduction of the corresponding ketones
5, 7, 11–13, 24
, and
25
using the chiral borane reagent chlorodiisopinocampheylborane [(I
pc
)
2
BCl]. Nickel(0)‐mediated coupling of bromopyridines
2, 15
, and
31
gives
C
2
‐symmetric 2,2′‐bipyridines (
R,R
)‐
32
, (
R,R′
)‐
33
, and (
S,S
)‐
38
, respectively, which form metal complexes with Co
II
, Pd
II
, Cu
I
, and Ag
I
. Aryl‐substituted pyridines
26
, and
39–41
are synthesized by palladium(0)‐catalyzed cross couplings of
2
and
15
with boronic acids
42–44
.</abstract><doi>10.1002/cber.19921250528</doi><tpages>22</tpages></addata></record> |
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| ispartof | Chemische Berichte, 1992-05, Vol.125 (5), p.1169-1190 |
| issn | 0009-2940 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_cber_19921250528 |
| source | Wiley Online Library All Journals |
| title | Enantioselective Synthesis of Optically Active Pyridine Derivatives and C 2 ‐Symmetric 2,2′‐Bipyridines |
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