Synthesis of Chiral 1-Substituted Tetrahydroisoquinolines by the Intramolecular 1,3-Chirality Transfer Reaction Catalyzed by Bi(OTf)3

被引：37

作者：

Kawai, Nobuyuki ^{[1
]}

Abe, Ryuzou ^{[1
]}

Matsuda, Mika ^{[1
]}

Uenishi, Jun'ichi ^{[1
]}

机构：

[1] Kyoto Pharmaceut Univ, Yamashina Ku, Kyoto 6078412, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 07期

基金：

日本学术振兴会;

关键词：

ALLYLIC ALCOHOLS; ASYMMETRIC-SYNTHESIS; DIRECT SUBSTITUTION; IMINIUM IONS; AMINATION; FORMAMIDINES; CONDENSATION; SULFONAMIDES; HETEROCYCLES; ALKYLATION;

D O I：

10.1021/jo102452d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The intramolecular 1,3-chirality transfer reaction of chiral amino alcohols 1 with 99% ee was developed to construct chiral 1-substituted tetrahydroisoquinoline 2. Bi(OTf)(3) (10 mol%)-catalyzed cyclization of 1 (R=H) afforded (S)-1-(E)-propenyl tetrahydroisoquinoline 2 (R=H) in 83% yield with a ratio of 98:2. The stereochemistry at the newly formed chiral center was produced by a syn S(N)2'-type process. In this reaction, the substituent on the benzene ring of 1 significantly affected the reactivities and selectivities. A plausible reaction mechanism was proposed.

引用

页码：2102 / 2114

页数：13

共 50 条

[1] Lewis acid-catalyzed intramolecular amination via 1,3-chirality transfer
Kawai, Nobuyuki
Abe, Ryuzou
Uenishi, Jun'ichi
[J]. TETRAHEDRON LETTERS, 2009, 50 (47) : 6580 - 6583
[2] Stereochemistry and construction of tetrasubstituted chiral carbon Centers in intramolecular Pd-catalyzed 1,3-chirality transfer reactions
Kawai, Nobuyuki
Lagrange, Jean-Marie
Uenishi, Jun'ichi
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (17) : 2808 - 2814
[3] Palladium-catalyzed stereospecific synthesis of 2,6-disubstituted tetrahydropyrans: 1,3-chirality transfer by an intramolecular oxypalladation reaction
Kawai, Nobuyuki
Lagrange, Jean-Marie
Ohmi, Masashi
Uenishi, Jun'ichi
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (12): : 4530 - 4537
[4] Stereochemistry of Intermolecular Oxypalladation: PdII-Catalyzed 1,3-Chirality Transfer Reaction of Chiral Allylic Alcohol with Methanol
Vikhe, Yogesh S.
Hande, Sudhir M.
Kawai, Nobuyuki
Uenishi, Jun'ichi
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15): : 5174 - 5180
[5] An Efficient Synthesis of 2- and 2,6-Substituted Piperidines Using PdII-Catalyzed 1,3-Chirality Transfer Reaction
Hande, Sudhir M.
Kawai, Nobuyuki
Uenishi, Jun'ichi
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (01): : 244 - 253
[6] SYNTHESIS OF DIHYDROISOQUINOLINES AND 1-SUBSTITUTED TETRAHYDROISOQUINOLINES
SCULLY, FE
SCHLAGER, JJ
[J]. HETEROCYCLES, 1982, 19 (04) : 653 - 656
[7] AN EFFICIENT SYNTHESIS OF CHIRAL QUATERNARY CARBON CENTERS WITH HIGH OPTICAL PURITY VIA 1,3-CHIRALITY TRANSFER
IBUKA, T
TANAKA, M
NISHII, S
YAMAMOTO, Y
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (20) : 1596 - 1598
[8] PdII-Catalyzed Cascade Reaction with 1,3-Chirality Transfer; Stereoselective Synthesis of Chiral Nonracemic 2,2′-THF-THF Ring Units
Uenishi, Jun'ichi
Fujikura, Yuhei
Kawai, Nobuyuki
[J]. ORGANIC LETTERS, 2011, 13 (09) : 2350 - 2353
[9] Enantioselective Synthesis of 1-Substituted 1,2,3,4-Tetrahydroisoquinolines through 1,3-Dipolar Cycloaddition by a Chiral Phosphoric Acid
Jin, Yuan
Honma, Yasuhiro
Morita, Hisashi
Miyagawa, Masamichi
Akiyama, Takahiko
[J]. SYNLETT, 2019, 30 (13) : 1541 - 1545
[10] SYNTHESIS OF SOME DERIVATIVES OF 1-SUBSTITUTED TETRAHYDROISOQUINOLINES
LEVI, M
IVANOV, C
DRYANSKA, M
PAVLOVA, A
[J]. KHIMIKO-FARMATSEVTICHESKII ZHURNAL, 1971, 5 (02): : 33 - &

← 1 2 3 4 5 →