Directed reduction of β-amino ketones to syn or anti 1,3-amino alcohol derivatives

被引:68
作者
Keck, GE [1 ]
Truong, AP [1 ]
机构
[1] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA
关键词
D O I
10.1021/ol026456y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The reduction of beta-amino ketones with samarium(II) iodide has been investigated. Either the syn or anti 1,3-amino alcohols can be obtained as the major product due to a divergence in selectivity with different N-protecting groups.
引用
收藏
页码:3131 / 3134
页数:4
相关论文
共 15 条
[1]   STEREOSELECTIVE SYNTHESIS OF 1,3-AMINO ALCOHOLS AND 1,3-AMINO KETONES [J].
BARLUENGA, J ;
AGUILAR, E ;
FUSTERO, S ;
OLANO, B ;
VIADO, AL .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (04) :1219-1223
[2]   TOTAL SYNTHESIS OF K-13 [J].
BOGER, DL ;
YOHANNES, D .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11) :2498-2502
[3]   Enantioselective mannich-type reactions using a novel chiral zirconium catalyst for the synthesis of optically active β-amino acid derivatives [J].
Ishitani, H ;
Ueno, M ;
Kobayashi, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) :8180-8186
[4]   The first directed reduction of β-alkoxy ketones to anti-1,3-diol monoethers:: Identification of spectator and director alkoxy groups [J].
Keck, GE ;
Wager, CA .
ORGANIC LETTERS, 2000, 2 (15) :2307-2309
[5]   CATALYTIC ASYMMETRIC ALLYLATION REACTIONS .3. EXTENSION TO METHALLYLSTANNANE, COMPARISON OF PROCEDURES, AND OBSERVATION OF A NONLINEAR EFFECT [J].
KECK, GE ;
KRISHNAMURTY, D ;
GRIER, MC .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (24) :6543-6544
[6]   An especially convenient stereoselective reduction of β-hydroxy ketones to anti 1,3 diols using samarium diiodide [J].
Keck, GE ;
Wager, CA ;
Sell, T ;
Wager, TT .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2172-2173
[7]   Catalytic asymmetric synthesis of antimalarial alkaloids febrifugine and isofebrifugine and their biological activity [J].
Kobayashi, S ;
Ueno, M ;
Suzuki, R ;
Ishitani, H ;
Kim, HS ;
Wataya, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18) :6833-6841
[8]   OXIDATIVE N-DEARYLATION OF 2-AZETIDINONES - PARA-ANISIDINE AS A SOURCE OF AZETIDINONE NITROGEN [J].
KRONENTHAL, DR ;
HAN, CY ;
TAYLOR, MK .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (14) :2765-2768
[9]  
Molander G.A., 1995, ORGANIC REACTIONS, V46, P211, DOI DOI 10.1002/0471264180.OR046.03
[10]   STEREOSELECTIVE PREPARATION OF ACYCLIC SYN-BETA-AMINO ALCOHOLS FROM BETA-HYDROXY KETONES VIA THE CORRESPONDING O-BENZYL OXIMES [J].
NARASAKA, K ;
UKAJI, Y ;
YAMAZAKI, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (02) :525-533