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A convenient synthesis of 2-methoxy-1-naphthyl sulfoxides in high enantiomeric purity. A new asymmetric synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines

โœ Scribed by Stephen G. Pyne; A.R. Hajipour; K. Prabakaran

Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
277 KB
Volume
35
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

The synthesis of Qastaeomerieally pure (-)_(S) ~lhyl 2-metboxy-l-naphthalenesulfurab (5) is (+)-(R) benzyl zmethoxy+napbthy1 sulfoxidc. (7) and (8) rcspd't?y. in hi@ coimtiomeric ~&h&d (8) &erg-additkm IO 6,7-dSmetboxy-3.4diby N-oxide (2) to give a l-be=@-i23.~ tetranydroisoq~ ddvative (9) with bigb product ykxtial (d. r. 96 : 4). The StmochQnirtry of (9) wasde&xmiibyasiaglccqstalX-rayrtruaurcdetemunatl . Sulfoxides are versatile compound8 for organic synthesis and asymmetric synthe8is.l The 1.2-and 1 &addition n~actions of traditional lithiated alkyl and bcnzyl ptolyl sulfoxides to carbonyl compound8 and Michael acceptors however, is generally poorly diastereoselective.* We and others have shown that a much

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## A diastereoselective addition of Grignard reagents to nonracemic 2-(I-naphthyl)4-(4R)-phenyl-I.3-oxazolidines (1) followed by electrophilic trapping of the azaenokzte is described. This tandem addition was perjormed in a single flask producing I, I,2-trisubstituted 1.2-dihydronaphthalenes 7 in