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Extra resources for Compendium of Organic Synthetic Methods Volume 5
I, Organometallics, 8 0% 1,1651 (1982) 32 COMPENDIUM OF ORGANIC SYNTHETIC METHODS V O L 5 m T i (NEt2)3 0-C- N (LPr ) II 0 OCb Angew Chem Int Ed, SiMe - CH3CH0 TiC14, CH2C12 JACS, MgCl t Cp2ZrC1 SECTION 348 CHO 21, 372 (1982) OH - -Ph v -c m3 104,4963 76% 86% ee (1982) -+ OH 90% 88% threo Tetr Lett, 22, 2895 (1981) SECTION 348 33 N U C L E O P H I L I C ADDITIONS TO ALDEHYDES, FORMING ALCOHOLS Tetr L e t t , Ph-CHO CrC13, LiA1H4 t Br w Ph t - _c"3 96% 100% threo or CrCl Tetr L e t t , w1 23, 3497 (1982) 2, 1037 (1981) OH 1 ) Sn, THF 2 ) H20 Ph -CHO Ph Chem L e t t , 1527 (1981) 34 COMPENDIUM OF O R G A N I C SYNTHETIC METHODS VOL 5 Me0 PhCHO 4H Ph A1 E t 2 SECTION 348 "H 83% Me0 vi2 JCS Chem Comm, 845 (1982) PhCHO Me\ - Ph 73% Me N-NMe2 1 T i (O-i-Pr)3 Angew Chem I n t Ed, 21, 864 (1982) Me2CuLi $CHO OCH 2O Bz BzOCH20 OH >20:1 d i a s t e r e o s e l e c t i v i t y Tetr Lett, 21, 1031 and 1035 (1980) CH3CH2CN t Bu2BOTf i -Pr2NEt * ;H3 Ph-CH-CH-CN bH Ph-CHO Chem L e t t , 1401 (1982) 90% S E C T I O N 348 N U C L E O P H I L I C A D D I T I O N S TO ALDEHYDES, 35 FORMING ALCOHOLS - OMe t THF O C u H OMe 90% OH O JACS, 102, 6900 (1980) PhCHO + 1 ) Zn, THF 2) H k , - O 0T H P p * Ph-CH-CMe2COOH I 88% OH Bull SOC C h i m F r a n c e 11, 145 (1980) L iCfC-TMS C h e m L e t t , 255 (1980) 36 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 5 ‘0 O ‘ Ac C-HO S E C T I O N 34B ____t TiC14 OH 60% Tetr Lett, 34C: 22, 3269 (1981) C o u p l i n g o f A l d e h y d e s t o G i v e Diols 2 Ph-CHO 1 ) Fe(C0)5, p y r i d i n e e 88% Ph-CH-CH-Ph dH 6 H 2 ) H30Q Chem L e t t , 1141 (1980) 2 Ph-CHO TiC13 NaOH OH I OH 1 Ph-F-F-Ph k i i Tetr Lett, R e l a t e d methods: 3 , 3517 A l c o h o l s f r o m Ketones ( S e c t i o n 4 2 ) (1982) SECTION 37 37 ALCOHOLS FROM AMINES S e c t i o n 35 Alcohols and Phenols from A 1 k y l s , Methylenes and Aryls No examples of t h e r e a c t i o n R R ' ROH ( R ' = a l k y l , a r y l , e t c .
16 C O M P E N D I U M OF O R G A N I C SYNTHETIC METHODS V O L 5 S y n t h Comm, Q OQ S E C T I O N 23 12, 855 (1982) c - 0CMe c 1 ) CF3S020TMS 98% 2 ) H20 ONe OMe S y n t h e s i s , 545 ( 1 9 8 0 ) PhSeH, NaH SePh TH F/ HrlPA 96% JOC, 46, 2605 (1981) O t h e r r e a c t i o n s u s e f u l f o r t h e h y d r o l y s i s o f e s t e r s may be f o u n d i n S e c t i o n 30A ( P r o t e c t i o n o f C a r b o x y l i c A c i d s ) . C. Tetr Lett, - 1 ) i--PrHgBr, CuCl 2) H20, 22, 96% 1013 (1981) COOH w i-Pr B u l l Chem SOC Japan, 55, 3555 78% (1982) Chem L e t t , 571 (1980) t 2) H3d9 * Bu-CH2CH2COOH Bu2CuMgB r Tetr Lett, Tetr Lett, 21, 935 (1980) 21, 2181 (1980) 92% 18 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 5 SECTION 25 94% Chem L e t t , 651 ( 1 9 8 0 ) 1 ) BuLi yH2Ph 2 ) g-C8H,7Br 'PH3 3 ) NaOH, H20 N n-C8H, 7COOH 4 ) H30t Tetr Lett, Also via: Esters - 22, 261 (1981) S e c t i o n 115 S e c t i o n 26 C a r b o x y l i c A c i d s f r o m H y d r i d e s 0 S y n t h e s i s , 74 (1981) 66% SECTION 29 19 C A R B O X Y L I C ACIDS FROM OLEFINS S e c t i o n 27 Carboxylic Acids from Ketones Mo(acac)2 OTMS 86'2 t-BuOOH Tetr Lett, Bu4N@104 0 II Ph-C-CH,Br L 2, 2595 (1981) o * Ph-COOH dioxane 7 5% S y n t h e s i s , 563 (1980) Also v i a : Esters - Section 117.
Z. Chem, 188 (1981) PROTECTION OF CARBOXYLIC ACIDS SECTION 30A 0 R-C-0-CH2 21 Na2S204 +R-COOH H 20/Me CN Synth Comm, 85-95% 12, 219 (1982) v Br-CH2 eMOOC@- 0 I1 R-C-ONa - n R-I-OCH, -(ot COOMe JCS Chem Comm, 1083 (1980) Angew Chem Int Ed, 2J, 780 (1982) rs R-C-OH CH2=CH-CH2SiMe3 0 + It R-C-OSiMe3 Tetr Lett, 1 ,835 (1980) nJ 90% COMPENDIUPI OF ORGANIC SYNTHETIC METHODS VOL 5 22 Me Si C 1 R-COOH R = C1 CH2CH2C1 - 0 II R-C-OSiMe3 SECTION 30A %70-90% alkyl , vinyl, ally1 , acetylenic, etc. Synthesis, 626 (1980) 0 (Me3Si)20 II R-C-OH H2S04 0 It e R-C-OSiMe3 '~70-90% Chem Lett, 1475 (1980) Ph 8 R-C-OH It 0 Chem Lett, 1551 (1981) SECTION 30A PROTECTION OF CARBOXYLIC ACIDS 23 The 5,6-dihydrophenanthridine protecting group may be activated and removed by oxidation: Ce+4, H20 cef4, C ~ O R'NH2 + + R-COOH 0 II R-C-NHR ' Chem Lett, 991 (1982) NaHS Used as a C-terminal protecting group in peptide synthesis.