309929-19-9

Basic information

• Product Name: (2R,4R)-2-((S)-7-Bromo-1-methylene-1,2,3,4-tetrahydro-naphthalen-2-yl)-4-ethyl-3-(toluene-4-sulfonyl)-oxazolidine
• Synonyms: (2R,4R)-2-((S)-7-Bromo-1-methylene-1,2,3,4-tetrahydro-naphthalen-2-yl)-4-ethyl-3-(toluene-4-sulfonyl)-oxazolidine
• CAS NO: 309929-19-9
• Molecular Weight: 476.434
• Mol File: 309929-19-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,4R)-2-((S)-7-Bromo-1-methylene-1,2,3,4-tetrahydro-naphthalen-2-yl)-4-ethyl-3-(toluene-4-sulfonyl)-oxazolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4R)-2-((S)-7-Bromo-1-methylene-1,2,3,4-tetrahydro-naphthalen-2-yl)-4-ethyl-3-(toluene-4-sulfonyl)-oxazolidine(309929-19-9)
• EPA Substance Registry System: (2R,4R)-2-((S)-7-Bromo-1-methylene-1,2,3,4-tetrahydro-naphthalen-2-yl)-4-ethyl-3-(toluene-4-sulfonyl)-oxazolidine(309929-19-9)

Safety Data

• Hazardous Substances Data: 309929-19-9(Hazardous Substances Data)

Upstream product

• 309929-09-7 ((7-bromo-3,4-dihydronaphthalen-1-yl)oxy)trimethylsilane 
• 32281-97-3 7-bromo-3,4-dihydro-2H-naphthalen-1-one 
• 309929-11-1 [2R,2(2R,4R)]-7-Bromo-2-{4-ethyl-3-[(4-methylbenzene)sulfonyl]-1,3-oxazolidin-2-yl}-1,2,3,4-tetrahydro-1-naphthalenone 

Downstream Products

• 309929-35-9 (1S,2S,2(2R,4R))-7-Bromo-2-{4-ethyl-3-[(4-methylbenzene)sulfonyl]-1,3-oxazolidin-2-yl}-1,2,3,4-tetrahydro-1-naphthylmethanol 

Relevant articles and documents

Asymmetric synthesis of stereodefined 7-(alk-1-enyl)-5,6,7,8- tetrahydronaphthalene-2-carboxylic acids and their precursors, bearing a polar group in the 8-position, by the 3-sulfonyl-1,3-oxazolidine method

7-Bromo-1-(trimethylsilyloxy)-naphthalene 2 was subjected to asymmetric formylation by means of (R)-4-ethyl-2-methoxy-3-tosyl-1,3-oxazolidine (1). The enantiomerically pure 1-tetralones u-3 and l-3, bearing a masked formyl group, were elaborated diastereoselectively to achieve the title compounds 11, 13 and 23 by transformation of the l-oxo group to a tertiary methyl carbinol moiety or a hydroxymethyl group. Subsequently, the formyl group was converted to a long-chain alkene moiety and, finally, the carboxyl group was introduced via bromine-lithium exchange and carboxylation. Difficulties arose from the high dehydration tendencies of the intermediate tertiary alcohols and by facile epimerisation of the free hydroxyaldehydes. With examples for further application of similar strategies it is demonstrated how these problems could be solved.