Toward the creation of NMR Databases in chiral solvents: Bidentate chiral NMR solvents for assignment of the absolute configuration of acyclic secondary alcohols

被引：61

作者：

Kobayashi, Y ^{[1
]}

Hayashi, N ^{[1
]}

Kishi, Y ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 03期

关键词：

D O I：

10.1021/ol0171160

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The absolute configuration of acyclic secondary alcohols can be established from analysis of the chemical shift behaviors of the adjacent carbons in bidentate chiral solvents (R,R)- and (S,S)-1d as formulated in the boxed illustration.

引用

页码：411 / 414

页数：4

共 17 条

[1] Synthesis and X-ray crystal structure of N,N-bis[(S)-1-phenylethyl]-(R,R)-4,5-diamino-1,7-octadiene [J].

Alvaro, G ;

Grepioni, F ;

Savoia, D .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) :4180-4182

[2] SIMPLE SYNTHESIS OF A C-2 SYMMETRICAL VICINAL DIAMINE - HIGHLY DIASTEREOSELECTIVE GRIGNARD ADDITION TO A CHIRAL BIS-IMINE [J].

BAMBRIDGE, K ;

BEGLEY, MJ ;

SIMPKINS, NS .

TETRAHEDRON LETTERS, 1994, 35 (20) :3391-3394

[3] Asymmetric synthesis of 1,2-diamino-4,5-dimethylcyclohexanes by zirconium-catalyzed and -promoted reductive cyclization reactions [J].

Grepioni, F ;

Grilli, S ;

Martelli, G ;

Savoia, D .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3679-3683

[4] Toward the creation of NMR databases in chiral solvents for assignments of relative and absolute stereochemistry: Scope and limitation [J].

Hayashi, N ;

Kobayashi, Y ;

Kishi, Y .

ORGANIC LETTERS, 2001, 3 (14) :2249-2252

[5] Hydrogen shifts in cyclohexylcarbenes. Spatial dependence of activating power and of primary deuterium isotope effects. [J].

Kenar, JA ;

Nickon, A .

TETRAHEDRON, 1997, 53 (44) :14871-14894

[6]

Kobayashi Y, 2000, ANGEW CHEM INT EDIT, V39, P4279, DOI 10.1002/1521-3773(20001201)39:23<4279::AID-ANIE4279>3.0.CO

[7]

2-R

[8]

Kobayashi Y, 2000, HELV CHIM ACTA, V83, P2562, DOI 10.1002/1522-2675(20000906)83:9<2562::AID-HLCA2562>3.0.CO

[9]

2-Z

[10] Toward the creation of NMR databases in chiral solvents for assignments of relative and absolute stereochemistry: NMR desymmetrization of meso compounds [J].

Kobayashi, Y ;

Hayashi, N ;

Kishi, Y .

ORGANIC LETTERS, 2001, 3 (14) :2253-2255

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