Synthesis of (R)- or (S)-diphenylphosphinoyl hydroxy aldehydes and 1,2-diols using Mukaiyama's bicyclic aminal methodology and Sharpless asymmetric dihydroxylation

被引：12
作者：
OBrien, P [1 ]
Warren, S [1 ]
机构：
[1] UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CB2 1EW,ENGLAND
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1996年 / 17期
关键词：
D O I：
10.1039/p19960002129
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two different approaches to diphenylphosphinoyl hydroxy aldehydes and 1,2-diols are compared. A lengthy chiral auxiliary approach using proline-derived aminals enables hydroxy aldehydes and 1,2-diols of known absolute stereochemistry and high enantiomeric excess to be synthesised, In contrast, a much shorter asymmetric dihydroxylation route generates 1,2-diols with lower enantiomeric excesses and unexpected (in view of Sharpless's mnemonic) absolute stereochemistry. The dihydroxylation results are thus of both mechanistic and synthetic value.
引用
收藏
页码：2129 / 2138
页数：10
相关论文
共 50 条
[31]   (S)-(+)-NEOMENTHYLDIPHENYLPHOSPHINE IN NICKEL-CATALYZED ASYMMETRIC REDUCTIVE COUPLING OF ALKYNES AND ALDEHYDES: ENANTIOSELECTIVE SYNTHESIS OF ALLYLIC ALCOHOLS AND alpha-HYDROXY KETONES [(R)-Butan-2-one, 1-cyclohexyl, 1-hydroxy-] [J].
Van Dyke, Aaron R. ;
Miller, Karen M. ;
Jamison, Timothy F. .
ORGANIC SYNTHESES, 2007, 84 :111-+
[32]   STEREOSELECTIVE SYNTHESIS OF 3-AMINO 1,2-DIOLS VIA INTERMOLECULAR PINACOL CROSS-COUPLING OF ALPHA-[(ALKOXYCARBONYL)AMINO] ALDEHYDES WITH ALIPHATIC-ALDEHYDES - SHORT ASYMMETRIC SYNTHESES OF 2 2,3,6-TRIDEOXY-3-AMINO SUGARS [J].
KONRADI, AW ;
PEDERSEN, SF .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) :4506-4508
[33]   Design, synthesis and asymmetric 1,2-addition reactions of oxazolidines derived from (1R,2S)-Ephedrine and (1S,2S)-Pseudoephedrine [J].
Parrott, Raleigh W., II ;
Hitchcock, Shawn R. .
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
[34]   Remote stereocontrol by the sulfinyl group:: Mukaiyama aldol reactions of (S)-2-[2-(p-tolylsulfinyl)phenyl]acetaldehyde in the asymmetric synthesis of β-hydroxyacids and 1,3-diols [J].
Ruano, Jose L. Garcia ;
Fernandez-Ibanez, M. Angeles ;
Maestro, M. Carmen .
TETRAHEDRON, 2006, 62 (52) :12297-12305
[35]   (R)- and (S)-3-Hydroxy-4,4-dimethyl-1-phenyl- 2- pyrrolidinone as chiral auxiliaries for the asymmetric synthesis of a-hydroxy acids [J].
Camps, P. ;
Perez, F. ;
Soldevilla, N. .
Tetrahedron: Asymmetry, 8 (11)
[36]   (R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone as chiral auxiliaries for the asymmetric synthesis of alpha-hydroxy acids [J].
Camps, P ;
Perez, F ;
Soldevilla, N .
TETRAHEDRON-ASYMMETRY, 1997, 8 (11) :1877-1894
[37]   2-{(4a′S,6a′S,10a′R,10b′R)-Octahydrospiro[1,3-dioxolane-2,2′-pyrano[2,3-c]chromen]-6a′(1′H)-yloxy}ethanol in the Synthesis of (2S)- and (2R)-Dodecane-1,2-diols [J].
Faizullina, L. Kh. ;
Tagirov, A. R. ;
Salikhov, Sh. M. ;
Petrova, S. F. ;
Valeev, F. A. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (10) :1840-1843
[38]   2-{(4a′S,6a′S,10a′R,10b′R)-Octahydrospiro[1,3-dioxolane-2,2′-pyrano[2,3-c]chromen]-6a′(1′H)-yloxy}ethanol in the Synthesis of (2S)- and (2R)-Dodecane-1,2-diols [J].
L. Kh. Faizullina ;
A. R. Tagirov ;
Sh. M. Salikhov ;
S. F. Petrova ;
F. A. Valeev .
Russian Journal of Organic Chemistry, 2020, 56 :1840-1843
[39]   Asymmetric syntheses of (1R,1′R,5′R,7′R) and (1S,1′R,5′R,7′R)-1-hydroxy-exo-brevicomin and a formal synthesis of (+)-exo-brevicomin [J].
Kumar, DN ;
Rao, BV .
TETRAHEDRON LETTERS, 2004, 45 (10) :2227-2229
[40]   Synthesis of 10b(R)-hydroxypancratistatin, 10b(S)-hydroxy-1-epipancratistatin, 10b(S)-hydroxy-1,2-diepipancratistatin and related isocarbostyrils [J].
Pettit, GR ;
Melody, N ;
Herald, DL ;
Schmidt, JM ;
Pettit, RK ;
Chapuis, JC .
HETEROCYCLES, 2002, 56 (1-2) :139-155
12345