- Application of the sulfonamide functional groups as an anchor for solid phase organic synthesis (SPOS)
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Sulfonyl chlorides have been found to readily couple to an amino functionalized resin. The resulting sulfonamide anchoring group is stable to a variety of reactions commonly used in SPOS. Acid induced cleavage is facile, affording functionalized sulfonamides in high yields.
- Beaver,Siegmund,Spear
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p. 1145 - 1148
(2007/10/03)
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- Camphor-Derived N-Acryloyl and N-Crotonoyl Sultams: Practical Activated Dienophiles in Asymmetric Diels-Alder Reactions
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Starting from (+)-camphor-10-sulfonyl chloride (5), the crystalline sultam 8 was easily prepared.Lewis-acid-promoted Diels-Alder additions of the crystalline N-acryloyl and N-crotonoyl derivatives 9 and 10, respectively, to cyclopentadiene and 1,3-butadiene at -130 to -78 grad furnished adducts 11, 12 and 17 with high chiral efficiency.Crystallization of the adducts and nondestructive removal of 8 gave either alcohols 13, 14 and 18 or acid 19 in 99percent enantiomeric purity.The sense of induction was reversed on using the enantiomer of 8 as the auxiliary.The structure of 10 was established by X-ray diffraction analysis
- Oppolzer, Wolfgang,Chapuis, Christian,Bernardinelli, Gerald
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p. 1397 - 1401
(2007/10/02)
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