Asymmetric Direct 1,2-Addition of Aryl Grignard Reagents to Aryl Alkyl Ketones

被引：18

作者：

Osakama, Kazuki ^{[1
]}

Nakajima, Makoto ^{[1
]}

机构：

[1] Kumamoto Univ, Grad Sch Pharmaceut Sci, Chuo Ku, 5-1 Oe Honmachi, Kumamoto 8620973, Japan

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 02期

关键词：

CATALYTIC ENANTIOSELECTIVE ADDITION; ACID-BASE CATALYSTS; TITANIUM(IV) CATALYST; ORGANOZINC REAGENTS; MAGNESIUM COMPLEXES; SECONDARY ALCOHOLS; ARYLBORONIC ACIDS; TERTIARY ALCOHOLS; CHIRAL LIGANDS; ALDEHYDES;

D O I：

10.1021/acs.orglett.5b03379

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective addition of Grignard reagents to ketones was promoted by a BINOL derivative bearing alkyl chains at the 3,3 '-positions. This is the first asymmetric direct aryl Grignard addition to ketones reported to date. A variety of tertiary diaryl alcohols could be obtained in high yields and enantioselectivities without using any other metal source.

引用

页码：236 / 239

页数：4

共 50 条

[1] Asymmetric Copper-Catalyzed Addition of Grignard Reagents to Aryl Alkyl Ketones
Madduri, Ashoka V. R.
Harutyunyan, Syuzanna R.
Minnaard, Adriaan J.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (13) : 3164 - 3167
[2] Remote induction of stereoselective 1,2-addition of aryl Grignard reagents to β-sulfinyl enones
Nakakita, Toshinori
Miura, Motofumi
Toriyama, Masaharu
Motohashi, Shigeyasu
Barybin, Mikhail V.
[J]. TETRAHEDRON LETTERS, 2014, 55 (05) : 1090 - 1092
[3] Copper(I) catalyzed asymmetric 1,2-addition of Grignard reagents to α-methyl substituted α,β-unsaturated ketones
Madduri, Ashoka V. R.
Minnaard, Adriaan J.
Harutyunyan, Syuzanna R.
[J]. CHEMICAL COMMUNICATIONS, 2012, 48 (10) : 1478 - 1480
[4] The stereochemistry of the 1,2-addition of Grignard reagents to some steroidal unsaturated ketones
Uyanik, C
Hanson, JR
Hitchcock, PB
[J]. JOURNAL OF CHEMICAL RESEARCH, 2003, (08) : 474 - 476
[5] Catalytic Enantioselective Addition of Aryl Grignard Reagents to Ketones
Fernandez-Mateos, Emilio
Macia, Beatriz
Yus, Miguel
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (29) : 6519 - 6526
[6] Addition of Grignard reagents to aryl acid chlorides: An efficient synthesis of aryl ketones
Wang, XJ
Zhang, L
Sun, XF
Xu, YB
Krishnamurthy, D
Senanayake, CH
[J]. ORGANIC LETTERS, 2005, 7 (25) : 5593 - 5595
[7] Asymmetric amplification in the catalytic enantioselective 1,2-addition of Grignard reagents to enones
Caprioli, Francesca
Madduri, Ashoka V. R.
Minnaard, Adriaan J.
Harutyunyan, Syuzanna R.
[J]. CHEMICAL COMMUNICATIONS, 2013, 49 (48) : 5450 - 5452
[8] Catalytic enantioselective alkyl and aryl addition to aldehydes and ketones with organozinc reagents derived from alkyl Grignard reagents or arylboronic acids
Hatano, Manabu
Gouzu, Riku
Mizuno, Tomokazu
Abe, Hitoshi
Yamada, Toshihide
Ishihara, Kazuaki
[J]. CATALYSIS SCIENCE & TECHNOLOGY, 2011, 1 (07) : 1149 - 1158
[9] Synthesis of cluster alkyl and aryl Grignard reagents in solution
Tjurina, LA
Smirnov, VV
Potapov, DA
Nikolaev, SA
Esipov, SE
Beletskaya, IP
[J]. ORGANOMETALLICS, 2004, 23 (06) : 1349 - 1351
[10] Catalytic Asymmetric Aryl Transfer Reactions to Aldehydes with Grignard Reagents as the Aryl Source
Muramatsu, Yusuke
Harada, Toshiro
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (34) : 10560 - 10563

← 1 2 3 4 5 →