Asymmetric synthesis of alkaloids using polyfunctionalized chiral building blocks

被引：22

作者：

Davis, FA ^{[1
]}

Chao, B ^{[1
]}

Andemichael, YW ^{[1
]}

Mohanty, PK ^{[1
]}

Fang, TN ^{[1
]}

Burns, DM ^{[1
]}

Rao, A ^{[1
]}

Szewczyk, JM ^{[1
]}

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

来源：

HETEROATOM CHEMISTRY | 2002年 / 13卷 / 05期

关键词：

D O I：

10.1002/hc.10090

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantiopure N-sulfinyl-delta-amino-beta-ketoesters and isoquinolones, prepared from sulfinimines (N-sulfinyl imines) are a new class of polyfunctionalized chiral building blocks. These building blocks provide easy access to enantiomerically pure, functionalized piperidines and tetrahydroisoquinolines with a minimum of chemical manipulation and protecting-group chemistry. (C) 2002 Wiley Periodicals, Inc.

引用

页码：486 / 492

页数：7

共 18 条

[1] Davis FA, 2000, SYNTHESIS-STUTTGART, P2106
[2] Intramolecular Mannich reaction in the asymmetric synthesis of polysubstituted piperidines: Concise synthesis of the dendrobate alkaloid (+)-241D and its C-4 epimer
Davis, FA
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[J]. ORGANIC LETTERS, 2001, 3 (20) : 3169 - 3171
[3] Asymmetric synthesis of 4-hydroxy-3-phenyltetrahydroisoquinolin derivatives using enantiopure sulfinimines (N-sulfinyl imines)
Davis, FA
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[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (23) : 8627 - 8634
[4] Sulfinimine-Mediated Asymmetric Synthesis of 1,3-Disubstituted Tetrahydroisoquinolines:: A Stereoselective Synthesis of cis- and trans-6,8-Dimethoxy-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline
Davis, FA
Mohanty, PK
Burns, DM
Andemichael, YW
[J]. ORGANIC LETTERS, 2000, 2 (24) : 3901 - 3903
[5] δ-amino β-keto esters, a designed polyfunctionalized chiral building block for alkaloid synthesis.: Asymmetric synthesis of (R)-(+)-2-phenylpiperidine and (-)-SS20846A
Davis, FA
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[J]. ORGANIC LETTERS, 2000, 2 (08) : 1041 - 1043
[6] Alkaloid synthesis using chiral δ-amino β-ketoesters:: A stereoselective synthesis of (-)-lasubine II
Davis, FA
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[7] Aza-Darzens asymmetric synthesis of N-(p-toluenesulfinyl) aziridine 2-carboxylate esters from sulfinimines (N-sulfinyl imines)
Davis, FA
Liu, H
Zhou, P
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[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (20) : 7559 - 7567
[8] Improved synthesis of enantiopure sulfinimines (thiooxime S-oxides) from p-toluenesulfinamide and aldehydes and ketones
Davis, FA
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Andemichael, Y
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[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) : 1403 - 1406
[9] Asymmetric synthesis of aziridine 2-phosphonates and azirinyl phosphonates from enantiopure sulfinimines
Davis, FA
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[J]. TETRAHEDRON LETTERS, 1999, 40 (02) : 249 - 252
[10] Asymmetric synthesis of α-methylphosphophenylalanine derivatives using sulfinimine-derived enantiopure aziridine-2-phosphonates
Davis, FA
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Titus, DD
[J]. ORGANIC LETTERS, 1999, 1 (07) : 1053 - 1055

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