e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Stereoselective Synthesis of anti??1, 4??Diols by a BH3⋅ THF??Mediated Rearrangement of 1, 2??Disubstituted Cyclobutenes

…, B Goldfuss, P Knochel

Index: Knapp, Kolja M.; Goldfuss, Bernd; Knochel, Paul Chemistry - A European Journal, 2003 , vol. 9, # 21 p. 5259 - 5265

Full Text: HTML

Citation Number: 15

Abstract

Abstract A new stereoselective rearrangement of cyclobutylboranes, obtained by the hydroboration of 1, 2-disubstituted cyclobutenes, provides anti-1, 4-diols with good-to- excellent diastereoselectivity. The mechanism of the rearrangement is discussed based on theoretical calculations.

PHENYLMAGNESIUM CHLORIDE Structure

PHENYLMAGNESIUM...

1,2-bis(phenylsulfonyl)-1-cyclobutene Structure

1,2-bis(phenyls...

~92%

[2-(benzenesulfonyl)cyclobuten-1-yl]benzene Structure

[2-(benzenesulf...

4-TRIFLUOROMETHYLPHENYLMAGNESIUMBROMIDE Structure

4-TRIFLUOROMETH...

1,2-bis(phenylsulfonyl)-1-cyclobutene Structure

1,2-bis(phenyls...

~71%

1-[2-(benzenesulfonyl)cyclobuten-1-yl]-4-(trifluoromethyl)benzene Structure

1-[2-(benzenesu...

Phenyllithium Structure

1-[2-(benzenesulfonyl)cyclobuten-1-yl]-4-methoxybenzene Structure

1-[2-(benzenesu...

~81%

1-methoxy-4-(2-phenylcyclobuten-1-yl)benzene Structure

1-methoxy-4-(2-...

4-Anisylmagnesium bromide Structure

4-Anisylmagnesi...

~%

1-methoxy-4-(2-phenylcyclobuten-1-yl)benzene Structure

1-methoxy-4-(2-...

1,2-bis(phenylsulfonyl)-1-cyclobutene Structure

1,2-bis(phenyls...

4-Anisylmagnesium bromide Structure

4-Anisylmagnesi...

~90%

1-[2-(benzenesulfonyl)cyclobuten-1-yl]-4-methoxybenzene Structure

1-[2-(benzenesu...

Phenyllithium Structure

1-[2-(benzenesulfonyl)cyclobuten-1-yl]-4-(trifluoromethyl)benzene Structure

1-[2-(benzenesu...

~77%

1-(2-phenylcyclobuten-1-yl)-4-(trifluoromethyl)benzene Structure

1-(2-phenylcycl...

4-TRIFLUOROMETHYLPHENYLMAGNESIUMBROMIDE Structure

4-TRIFLUOROMETH...

~%

1-(2-phenylcyclobuten-1-yl)-4-(trifluoromethyl)benzene Structure

1-(2-phenylcycl...

lithium,benzonitrile Structure

lithium,benzonitrile

[2-(benzenesulfonyl)cyclobuten-1-yl]benzene Structure

[2-(benzenesulf...

~69%

4-(2-phenylcyclobuten-1-yl)benzonitrile Structure

4-(2-phenylcycl...

PHENYLMAGNESIUM CHLORIDE Structure

PHENYLMAGNESIUM...

~%

4-(2-phenylcyclobuten-1-yl)benzonitrile Structure

4-(2-phenylcycl...

PHENYLMAGNESIUM CHLORIDE Structure

PHENYLMAGNESIUM...

~%

Benzene,1,1'-(1-cyclobutene-1,2-diyl)bis- Structure

Benzene,1,1'-(1...

Ethyllithium Structure

[2-(benzenesulfonyl)cyclobuten-1-yl]benzene Structure

[2-(benzenesulf...

~79%

(2-ethylcyclobuten-1-yl)benzene Structure

(2-ethylcyclobu...

PHENYLMAGNESIUM CHLORIDE Structure

PHENYLMAGNESIUM...

~%

(2-ethylcyclobuten-1-yl)benzene Structure

(2-ethylcyclobu...

zinc,propane Structure

[2-(benzenesulfonyl)cyclobuten-1-yl]benzene Structure

[2-(benzenesulf...

~73%

Benzene, [2-(1-methylethyl)-1-cyclobuten-1-yl]- (9CI) Structure

Benzene, [2-(1-...

PHENYLMAGNESIUM CHLORIDE Structure

PHENYLMAGNESIUM...

~%

Benzene, [2-(1-methylethyl)-1-cyclobuten-1-yl]- (9CI) Structure

Benzene, [2-(1-...

Phenyllithium Structure

[2-(benzenesulfonyl)cyclobuten-1-yl]benzene Structure

[2-(benzenesulf...

~85%

Benzene,1,1'-(1-cyclobutene-1,2-diyl)bis- Structure

Benzene,1,1'-(1...

Tert-Butyllithium Structure

Tert-Butyllithium

[2-(benzenesulfonyl)cyclobuten-1-yl]benzene Structure

[2-(benzenesulf...

~73%

(2-tert-butylcyclobuten-1-yl)benzene Structure

(2-tert-butylcy...

PHENYLMAGNESIUM CHLORIDE Structure

PHENYLMAGNESIUM...

~%

(2-tert-butylcyclobuten-1-yl)benzene Structure

(2-tert-butylcy...

5-Undecyne Structure

~%

1-butyl-2-pentylcyclobutene Structure

1-butyl-2-penty...