Enantiocontrolled synthesis of 2,3,6-trisubstituted piperidines using (η3-dihydropyridinyl)molybdenum complexes as chiral scaffolds.: Total synthesis of (-)-indolizidine 209B

被引：47

作者：

Shu, CT ^{[1
]}

Alcudia, A ^{[1
]}

Yin, JJ ^{[1
]}

Liebeskind, LS ^{[1
]}

机构：

[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2001年 / 123卷 / 50期

关键词：

D O I：

10.1021/ja011635g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantiopure TpMo(CO)(2)(pyridinyl) complexes were prepared using an efficient and scalable enzymatic kinetic resolution of the precursor to the molybdenum complex. A single TpMo(CO)2(pyridinyl) complex can function as a chiral scaffold for the enantiocontrolled synthesis of either 2,3,6-cis- or 2,6-cis-3-trans-trisubstituted piperidines. The synthetic potential of this methodology was demonstrated by a total synthesis of (-)-indolizidine 209B.

引用

页码：12477 / 12487

页数：11

共 20 条

[1] Enantiocontrolled synthesis of 2,3,6-trisubstituted piperidines using η3-dihydropyridinylmolybdenum complexes as chiral scaffolds:: A total synthesis of (-)-indolizidine 209B.
Shu, CT
Alcudia, A
Liebeskind, LS
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U112 - U112
[2] Diastereoselective Synthesis of 2,3,6-Trisubstituted Piperidines
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[3] STEREOSPECIFIC SYNTHESIS OF 2,3,6-TRISUBSTITUTED PIPERIDINES - AN EFFICIENT TOTAL SYNTHESIS OF (+/-)-PUMILIOTOXIN-C
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[4] (η3-Pyranyl)TpMo(CO)2 complexes as chiral scaffolds for the enantiocontrolled construction of 2,3,6-trisubstituted dihydropyrans (Tp = trispyrazolylborate)
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[5] Stereoselective approaches to 2,3,6-trisubstituted piperidines. An enantiospecific synthesis of quinolizidine (-)-217A
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[6] 1,4-bis(arylsulfonyl)dihydropyridines in synthesis. Enantioselective synthesis of 2,3,6-trisubstituted piperidines
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JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 624 (1-2) : 380 - 382
[7] ORGN 183-Enantiocontrolled synthesis of 2,2,6-trisubstituted tetrahydropyrans using η3-pyranylmolybdenum π-complexes as organometallic chirons
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ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
[8] Asymmetric Synthesis of 2,3,6-Trisubstituted Piperidines via Baylis-Hillman Adducts and Lithium Amide through Domino Reaction
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[9] Potent new NK1 antagonists from a modified piperidine template: Diastereoselective synthesis of 2,3,6-trisubstituted piperidines.
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[10] Novel synthesis of the main central 2,3,6-trisubstituted pyridine skeleton [Fragment A-B-C] of a macrobicyclic antibiotic, cyclothiazomycin
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