Asymmetric synthesis via chiral acetal templates. 8. Reactions with organometallic reagents

SD Lindell, JD Elliott, WS Johnson

Index: Lindell, Stephen D.; Elliott, John D.; Johnson, William S. Tetrahedron Letters, 1984 , vol. 25, # 36 p. 3947 - 3950

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Citation Number: 33

Abstract

The experimental procedure is typified by the following example. TiCl 4 (155 μl, 1.4 mmol) was added to a cold (−78°C) stirred solution of 1a (200 mg, 0.70 mmol) in dry CH 2 Cl 2 (20 ml). After 5 min a 2.8 solution of MeMgCl in THF (500 μl, 1.4 mmol) was instilled over a 10 min period. After a further 15 min a 2:1 MeOH:pyridine mixture 6 ml) was added, and the mixture was warmed to room temperature, then poured into 1 M hydrochloric acid. GC analysis (ref. 10) of the ...