Diastereoselective synthesis of pentasubstituted gamma-butyrolactones from silyl glyoxylates and ketones through a double Reformatsky reaction.

Diastereoselective synthesis of pentasubstituted gamma-butyrolactones from silyl glyoxylates and ketones through a double Reformatsky reaction.
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DOI:
10.1002/anie.200900215
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发表时间:
2009
影响因子:
16.6
通讯作者:
Johnson, Jeffrey S.
Johnson, Jeffrey S.
中科院分区:
化学1区
文献类型:
--
作者:
Greszler, Stephen N.;Johnson, Jeffrey S.

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Three contiguous stereocenterscan be established with remarkable diastereoselectivity in a double Reformatsky sequence. Densely functionalized γ‐butyrolactones were assembled rapidly by this approach, in which a ketone is used as the terminal electrophile (see scheme). Secondary transformations of the lactone products enhance their synthetic utility. R1=Me, H; R2=alkyl, aryl, CF3; Bn=benzyl, TBS=tert‐butyldimethylsilyl.
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