Department of Chemistry and Biochemistry, and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego, 9500 Gilman Drive MC0358, La Jolla, California 92093, USA.
Org Lett. 2010 Mar 19;12(6):1256-9. doi: 10.1021/ol1001126.
The addition of allyl stannanes to (S)-4,5-dihydro-5-phenyl-2H-oxazinone (3) was achieved under Brønsted acid catalysis to give 2-allylmorpholinones with high diastereoselectivity (up to dr 14.2:1). The product of dimethylallyltributylstannane addition to 3 was converted to l-beta-methylisoleucine, an alpha-amino acid residue found in the complex, biologically active marine-derived peptides polytheonamides A and B, and polydiscamides A-C.
烯丙基锡烷与(S)-4,5-二氢-5-苯基-2H-噁嗪酮(3)在布朗斯台德酸催化下加成,以高非对映选择性(高达 dr 14.2:1)得到 2-烯丙基吗啉酮。3 与二甲基烯丙基三丁基锡烷加成的产物转化为 l-β-甲基异亮氨酸,这是复杂的、具有生物活性的海洋衍生肽 polytheonamides A 和 B 以及 polydiscamides A-C 中的一种α-氨基酸残基。