Dynamic kinetic resolution of atropisomeric amides

被引：69

作者：

Chan, V ^{[1
]}

Kim, JG ^{[1
]}

Jimeno, C ^{[1
]}

Carroll, PJ ^{[1
]}

Walsh, PJ ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, P Roy & Diana T Vagelos Labs, Philadelphia, PA 19104 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 12期

关键词：

D O I：

10.1021/ol0492952

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Using L-proline as catalyst in the asymmetric aldol reaction and a series of benzamides and naphthamides, we have accomplished a dynamic kinetic resolution that simultaneously establishes the stereochemistry of the atropisomeric amide's chiral axis and a stereogenic center. The enantioselectivities ranged from 82% to 95% and the diastereoselectivities from 2.1:1 to 7.01.

引用

页码：2051 / 2053

页数：3

共 41 条

[1] Barriers to rotation about the chiral axis of tertiary aromatic amides
Ahmed, A
Bragg, RA
Clayden, J
Lai, LW
McCarthy, C
Pink, JH
Westlund, N
Yasin, SA
[J]. TETRAHEDRON, 1998, 54 (43) : 13277 - 13294
[2] Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions
Bahmanyar, S
Houk, KN
Martin, HJ
List, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) : 2475 - 2479
[3] The origin of stereoselectivity in proline-catalyzed intramolecular aldol reactions
Bahmanyar, S
Houk, KN
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (51) : 12911 - 12912
[4] Development of the first practical catalyst for the asymmetric addition of alkyl- and arylzinc reagents to ketones
Betancort, JM
García, C
Walsh, PJ
[J]. SYNLETT, 2004, (05) : 749 - 760
[5] Bolm C, 2001, ANGEW CHEM INT EDIT, V40, P3285
[6] Novel concepts in directed biaryl synthesis, part 78. The lactone concept: An efficient pathway to axially chiral natural products and useful reagents
Bringmann, G
Breuning, M
Tasler, S
[J]. SYNTHESIS-STUTTGART, 1999, (04): : 525 - 558
[7] Atropisomeric amides as chiral ligands: Using (-)-sparteine-directed enantioselective silylation to control the conformation of a stereogenic axis
Clayden, J
Johnson, P
Pink, JH
Helliwell, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (21) : 7033 - 7040
[8] (-)-Ephedrine as an auxiliary for the asymmetric synthesis of atropisomeric amides by dynamic resolution under thermodynamic control
Clayden, J
Lai, LW
[J]. TETRAHEDRON LETTERS, 2001, 42 (18) : 3163 - 3166
[9] Clayden J, 1999, ANGEW CHEM INT EDIT, V38, P2556, DOI 10.1002/(SICI)1521-3773(19990903)38:17<2556::AID-ANIE2556>3.0.CO
[10] 2-Q

← 1 2 3 4 5 →