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2005
Thiopyran derivatives
R 0370
Proline-Catalyzed Asymmetric Aldol Reactions of Tetrahydro-4H-thiopyranwith Aldehydes. — The asymmetric aldol reaction of tetrahydro-4H-thiopyr07- 125 -4-one
an-4-one (I) with aldehydes is efficiently catalyzed by L-proline giving preferentially
the anti-products (III). Desulfurization with hypophosphite and Raney-Ni is accompanied by some isomerization. Similar desulfurization of the diols derived from borane
reduction proceeds without loss of stereochemical integrity [cf. (V)]. — (WARD*, D.
E.; JHEENGUT, V.; Tetrahedron Lett. 45 (2004) 45, 8347-8350; Dep. Chem., Univ.
Saskatchewan, Saskatoon, Sask. S7N 5C9, Can.; Eng.) — Mais
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