Concept

Chiral auxiliary

Related publications (188)

Enhancement of benzylic basicity by a fluorine substituent at the para-position: a case of lone pair/lone pair repulsion

The introduction of a halogen atom at any arom. position of toluene considerably accelerates the base-promoted deprotonation of the Me group. P-Fluorotoluene is the only exception; proton abstraction from its benzylic site occurs approx. at one tenth of th ...

2000

Total asymmetric synthesis of doubly branched carba-hexopyranoses and amino derivatives starting from the Diels-Alder adducts of maleic anhydride to furfuryl esters

Pierre Vogel, Kurt Schenk

The Diels-Alder adducts of maleic anhydride to furfuryl esters were reduced into 7-oxabicyclo[2.2.l]hept-5-ene-1.2-exo,3-exo-trimethanol (+/-)-15 and enantiomerically pure (-)-15 (Scheme 1). The tripivalate of (+/-)-15 was converted into (1RS,2RS,3RS,4RS,5 ...

1999

Stereoselective synthesis of 5a-ethyl-1,2,3,3a,4,5,5a,6,9a,9b-decahydro-1,3,4-trihydroxy-3a-(hydroxym ethyl)-7H-benz[e]inden-7-one derivatives

Pierre Vogel

Homochiral Diels-Alder cyclodimerization of (+/-)-6-ethenyl-7-oxabicyclo[2.2.1]hept-5-en-2-endo-ol followed by oxidation gives (1RS,4RS,4aSR,4bSR,5RS,8RS,8aRS)-8a-ethenyl-1,3,4a,4b,5,6,8,8a,9-decahyd ro-11,4:5,8-diepoxyphenanthrene-2,7-dione (18). Selectiv ...

1999

Diastereoselective Synthesis of gamma -Hydroxy-beta -Amino Alcohols and (2S,3S)-beta -Hydroxyleucine from Chiral D-(N,N-Dibenzylamino)serine (TBDMS) Aldehyde

Jieping Zhu

Title serine deriv. I (TBDMS = tert-butyldimethylsilyl; Bn = benzyl) was synthesized from D-serine in excellent overall yield. The reactions of I with Grignard and organocerium reagents were highly stereoselective (Felkin model) to give gamma -hydroxy-beta ...

1998

Short, stereoselective syntheses of C(1 -> 3)-linked disaccharides

Pierre Vogel

Nucleophilic additions to D-isolevoglucosenone are face selective and generate the corresponding enolates which react with 1,2:3,4-di-O-isopropylidene-alpha-D-galacto-hexodialdo-1,5-pyranose to give aldol adducts. These can be reduced stereoselectively int ...

1998

Synthesis of C-linked imino disaccharides (=aza-C-disaccharides) with a pyrrolidine-3,4-diol moiety attached at C(3) of galactose via a hydroxymethylene linker and of a 7-(1,2,3-trihydroxypropyl)-octahydroxyindolizine-1,2,6,8-tetrol

Pierre Vogel

The lithium enolate of(+/-)-6-endo-chloro-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]heptan-2-o ne (16) added to furan-2-carboxaldehyde giving a single aldol 19 (Schemes 1 and 2) that was converted with high stereoselectivity into (+/-)-(1RS, 3SR,4SR,5RS,6SR) ...

1998

Combinatorial Diels-Alder approach to the synthesis of anti-tumor anthracyclines and analogues

Pierre Vogel

Doxorubicin has the widest spectrum of antitumor activity of all antineoplastic agents and is the most utilized anticancer drug worldwide. Unfortunately there are several tumor types that do not respond to doxorubicin and, furthermore, its effectiveness is ...

1998

Living polymers: Ab initio molecular dynamics study of the initiation step in the polymerization of isoprene induced by ethyl lithium

Ursula Röthlisberger

The polymn. of isoprene induced by alkyl lithium compds. in hydrocarbon solvents is known to proceed with a high stereoselectivity to (Z)-1,4-polyisoprene. We have studied the initiation step of this reaction with the help of ab initio mol. dynamics simula ...

1998

Stereoselective synthesis of new conduramines and aminocyclitol derivatives

Pierre Vogel

Triacetate of 7-oxabicyclo[2.2.1]hept-5-ene-1,2-exo,3-exo-trimethanol was converted selectively into (1RS,2SR,5RS,6RS)-4,5,6-tris(acetoxymethyl)-2-bromocyclohex-3-en-1-ol (4) or into (1RS,2SR,5RS,6RS)-5,6-bis(acetoxymethyl)-2-bromo-4-bromomethylcyclohex-3 ...

1998

A novel aldol condensation alternative: a,b-unsaturated aldehydes from 3-hydroxy-1-alkynes via dihydrodioxepins

The controlled aldol condensation between an aliph. ketone and an acetaldehyde equiv. remains a challenge. One soln. to this evergreen problem consists of the nucleophilic addn. of acetylene to the ketone and the subsequent isomerization of the resulting 3 ...

1998

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