Diastereoselective synthesis of (5R,7R)- and (5R,7S)-5,7-dimethyl-6,7-dihydro-5H-dibenz[c,e]azepines

被引：0

作者：

Saudan, LA ^{[1
]}

Bernardinelli, G ^{[1
]}

Kündig, EP ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland

来源：

SYNLETT | 2000年 / 04期

关键词：

diastereoselective imine alkylation; chiral azepine; Stille biaryl coupling; palladium; enantioselective lithiation;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Starting from (R)-1-(2-methoxyphenyl)ethylamine, the title compounds were synthesized, Key steps are a diastereoselective imine alkylation and a Pd-catalyzed biaryl coupling. The benzylic stereogenic centers of the (5R,7R)-azepine induce a strong bias for the atropisomeric conformer having aS axial chirality and pseudo equatorial Me groups.

引用

页码：483 / 486

页数：4

共 50 条

[1] A Concise and Efficient Synthesis of (5R,7S)-Kurzilactone and Its (5S,7R)-Enantiomer by the Mukaiyama Aldol Reaction
Sabitha, Gowravaram
Gopal, Peddabuddi
Reddy, C. Nagendra
Yadav, Jhillu S.
SYNTHESIS-STUTTGART, 2009, (19): : 3301 - 3304
[2] Enantioselective Route to 5-Methyl- and 5,7-Dimethyl-6,7-dihydro-5H-dibenz[c,e]azepine: Secondary Amines with Switchable Axial Chirality
Pira, Silvain L.
Wallace, Timothy W.
Graham, Jonathan P.
ORGANIC LETTERS, 2009, 11 (07) : 1663 - 1666
[3] A stereoselective approach for the total synthesis of (5R,7R,9R)-7,9-dihydroxy-5-decanolide
Manikanta, Gembali
Krishna, Palakodety Radha
TETRAHEDRON LETTERS, 2018, 59 (30) : 2893 - 2895
[4] Highly Concise and Stereoselective Total Synthesis of (5R,7S)-Kurzilactone
Mohapatra, Debendra K.
Karthik, Pulluri
Yadav, Jhillu S.
HELVETICA CHIMICA ACTA, 2012, 95 (07) : 1226 - 1230
[5] Synthesis of 6,7-dihydro-5H-dibenz[c,e]azepine
A. P. Stankevicius
L. N. Yanushene
Chemistry of Heterocyclic Compounds, 2006, 42 (11) : 1488 - 1489
[6] Stereoselective synthesis of (2R,5R)- and (2S,5R)-5-hydroxylysine
van den Nieuwendijk, AMCH
Kriek, NMAJ
Brussee, J
van Boom, JH
van der Gen, A
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2000, 2000 (22) : 3683 - 3691
[7] An asymmetric total synthesis of (+)-(3R,4S,5R,7S)-neoclansenamide
Wang, JQ
Tian, WS
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (02): : 209 - 212
[8] (1S,5R,7R,30S)-14-Deoxyisogarcinol
Kaur, Ranjeet
Vasudev, Prema G.
Chattopadhyay, Sunil K.
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O1861 - +
[9] A FACILE SYNTHESIS OF 6-ALKYL-6,7-DIHYDRO-5H-DIBENZ[C,E]AZEPINES - POTENT HYPOLIPIDEMICS
AKULA, MR
KABALKA, GW
SYNTHETIC COMMUNICATIONS, 1995, 25 (23) : 3901 - 3906
[10] Diastereoselective total synthesis of piperidine alkaloids: (2R,5R)-5-hydroxyhomopipecolic acid and (2R,5R,8R)-5-hydroxysedamine
Khobare, Sandip R.
Gajare, Vikas S.
Rajana, Nagaraju
Datrika, Rajender
Reddy, K. Srinivasa
Kumar, U. K. Syam
Siddaiah, Vidavalur
TETRAHEDRON LETTERS, 2015, 56 (17) : 2207 - 2210

← 1 2 3 4 5 →