Tetrahedron Letters p. 895 - 898 (1999)
Update date:2022-08-04
Topics:
Tamura, Osamu
Kuroki, Takahiro
Sakai, Yuta
Takizawa, Jun-ichi
Yoshino, Jun
Morita, Yasuhiro
Mita, Naka
Gotanda, Kentoku
Sakamoto, Masanori
(R)-5,6-Dihydro-5-phenyl-1,4-oxazin-2-one N-oxide {(R)-2 } reacts with allyl alcohols 3a-c in the presence of magnesium bromide from the less hindered face via exo-mode to afford corresponding cycloadducts 4a-c with excellent stereoselection. Treatment of (R)-2 with three equivalents of racemic secondary allyl alcohols 3d-g under the same conditions causes partial kinetic resolution to give 4d-g as main products among eight possible stereoisomers. Cycloadduct ent-4a from (S)-2 and 3a was converted directly to g-lactone 6, which is known as the key synthetic intermediate of antibiotic clavalanine.
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Doi:10.1002/(SICI)1521-3897(199902)341:2<121::AID-PRAC121>3.0.CO;2-D
(1999)Doi:10.1248/cpb.12.1271
(1964)Doi:10.1021/ja01023a037
(1968)Doi:10.1021/om9805988
(1999)Doi:10.1002/jccs.199900005
(1999)Doi:10.1016/S0008-6215(99)00044-0
(1999)