Double diastereoselective [3,3]-sigmatropic arz-Claisen rearrangemnts

被引：17

作者：

Davies, SG ^{[1
]}

Garner, AC ^{[1
]}

Nicholson, RL ^{[1
]}

Osborne, J ^{[1
]}

Savory, ED ^{[1
]}

Smith, AD ^{[1
]}

机构：

[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England

来源：

CHEMICAL COMMUNICATIONS | 2003年 / 17期

关键词：

D O I：

10.1039/b306323m

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Asymmetric [3,3]-sigmatropic aza-Claisen rearrangement of the (Z)-N-allyl-N,O-silylketene aminal of (3S,4E,alphaR)-1-benzyloxy-3-(N-propionyl-N-alpha-methylbenzylamino)hex-4-ene furnishes (2S,3R,4E,alphaR)-N-alpha-methylbenzyl-2,3-dimethyl-7-benzyloxyhept-4-enamide in > 92% d.e.; rearrangement of the diastereomeric (3R,4E,alphaR)-(Z)-N,O-silylketene aminal proceeds with low diastereoselectivity.

引用

页码：2134 / 2135

页数：2

共 18 条

[1] Asymmetric [3.3]-sigmatropic rearrangements in organic synthesis [J].

Enders, D ;

Knopp, M ;

Schiffers, R .

TETRAHEDRON-ASYMMETRY, 1996, 7 (07) :1847-1882

[2] A novel binaphthylamine auxiliary for asymmetric imidate Claisen rearrangement [J].

Hungerhoff, B ;

Metz, P .

TETRAHEDRON, 1999, 55 (52) :14941-14946

[3] Asymmetric claisen rearrangement [J].

Ito, H ;

Taguchi, T .

CHEMICAL SOCIETY REVIEWS, 1999, 28 (01) :43-50

[4] APPLICATION OF THE AZA-CLAISEN REARRANGEMENT TO THE TOTAL SYNTHESIS OF NATURAL-PRODUCTS - (-)-ISOIRIDOMYRMECIN [J].

ITO, S ;

TSUNODA, T .

PURE AND APPLIED CHEMISTRY, 1994, 66 (10-11) :2071-2074

[5] ASYMMETRIC INDUCTION IN THE CLAISEN REARRANGEMENT OF N-ALLYLKETENE N,O-ACETALS [J].

KURTH, MJ ;

DECKER, OHW ;

HOPE, H ;

YANUCK, MD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (02) :443-448

[6] CONCOMITANT C(ALPHA),C(BETA)-ASYMMETRIC INDUCTION IN THE AZA-CLAISEN REARRANGEMENT OF N-ALLYLKETENE N,O-ACETALS [J].

KURTH, MJ ;

DECKER, OHW .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (09) :1377-1383

[7] Highly enantioselective Claisen rearrangement of imidates derived from primary allyl alcohols [J].

Metz, P ;

Hungerhoff, B .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (13) :4442-4448

[8] VANADIUM-CATALYZED EPOXIDATIONS .2. HIGHLY STEREOSELECTIVE EPOXIDATIONS OF ACYCLIC HOMOALLYLIC ALCOHOLS PREDICTED BY A DETAILED TRANSITION-STATE MODEL [J].

MIHELICH, ED ;

DANIELS, K ;

EICKHOFF, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (25) :7690-7692

[9] Laboratory emulation of polyketide biosynthesis:: an iterative, aldol-based, synthetic entry to polyketide libraries using (R)- and (S)-1-(benzyloxy)-2-methylpentan-3-one, and conformational aspects of extended polypropionates [J].

Paterson, I ;

Scott, JP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (08) :1003-1014

[10] CONCERNING THE DIASTEREOFACIAL SELECTIVITY OF THE ALDOL REACTIONS OF ALPHA-METHYL CHIRAL ALDEHYDES AND LITHIUM AND BORON PROPIONATE ENOLATES [J].

ROUSH, WR .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4151-4157

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