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Synthesis of carbo- and aza-bicyclo[4.3.0] and [4.4.0] compounds by Ti(II)-mediated cyclization of 2,7- or 2,8-enynyl-1-ol derivatives

✍ Scribed by Yongcheng Song; Sentaro Okamoto; Fumie Sato


Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
75 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis


The reaction of 2,7-and 2,8-enynyl-1-ol derivatives where the ene moiety is a part of a ring with a Ti(O-i-Pr) 4 /2 i-PrMgCl reagent proceeds smoothly with excellent stereoselectivity to afford carbo-or aza-bicyclo[4.3.0] and [4.4.0] compounds, respectively, in high yields.


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Ti(II)-mediated cyclization of readily accessible optically active secondary 2,7-and 2,8-enyn-1-ol derivatives enables the selective preparation of any one of the four possible stereoisomers of the cyclized product with high optical purity.